One Lie to Live
by run-and-remember-me
Summary: A group of hunters from Men of Letters legacy families in the United States live together as undercover civilians in a bunker known as Omega. After a Man of Letters is injured on the job, Castiel Novak is assigned to Omega fresh out of training—to investigate Dean Winchester. Rating may change, but there won't be anything harsher than what we see on the CW.
1. Chapter 1

**A/N: Before you begin, I would like to note that this is based on the USA television series, Graceland, with a Supernatural spin. I do not have any rights to either Graceland or Supernatural, and this is an AU fanfiction.**

* * *

 **Chapter 1**

"I remember that day very clearly," Samuel Campbell began, addressing the crowd of initiates. "I was sitting right where you are sitting today. I was ready to knock down the door and kick some righteous ass. Just like you. I thought I was the smartest, the fastest, the best this institution had to offer."

Castiel Novak listened intently to the speech, thinking to himself: _If I can make it through one more lecture, I'll be free._ To think he was the best? Never. He knew how valuable his skillsets could be. He knew how far a 970 on his practical examinations could go. Castiel wouldn't be undercover as a pencil pusher for the government. He was going to be a real Man of Letters—not just some small-town detective scouring the strange columns of local news articles in hopes of finding a case.

"And then—then I stepped into the real world," Campbell continued. "We are here today to honor the newest initiates of The Men of Letters. I'm talking to you, ladies and gentlemen, because inside these walls, you all are the best of the best. But I just want to take just a moment to think about what's going to happen outside these walls..."

His authoritative voice was sincere, but besides his conviction, Castiel also noted a hint of regret. Perhaps his superior had experienced something in his time as a Man of Letters—something Castiel had yet to encounter.

"You all are walking off one battlefield in here and onto another battlefield out there. The difference being, the battlefield out there is real, and the dangers are real. Everything you've acquired of value in your short time on this earth, everything you are worth is locked inside of you, and that means, at this moment, you find yourself in the unique position you may never be in again: You have nothing to lose."

"I'll leave you with this," Campbell concluded. _There's a light at the end of this tunnel, after all,_ Castiel thought. "Whatever you think success means, I hope you'll stay open to the possibility that you've got it all wrong—that you have absolutely no idea what life has in store for you. You will make mistakes. You are not perfect. You will fail. And when the day comes that you figure it out, I hope you'll have the brains, the guts, and the straight up good luck to survive it. Congratulations. You are now members of the Men of Letters. Do me proud."

* * *

"Hey, Winchester!" Benny Lafitte yelled, pounding on the open door to Dean's room in the bunker. "Hey! Come on, time to get up, brother."

"Get out, Benny," Dean said weakly. His mind perked up within seconds as he realized how pathetic he just sounded, so he added, "I have a gun," for menacing effect.

The words seemed to have no effect on Benny. "Yeah? So do I. Come on, let's go. Now, is that cool? You told me no matter what you said or how ugly it got, not to let you sleep in, right?"

"I'd been awake thirty-two hours when I said that," Dean replied groggily.

"So what?" Benny said as he left the room. "No, if I let you nod off, you're just gonna yell at me 'cause I didn't do what you said. Let's go!"

Dean rolled back on his stomach miserably, moaning about how unfair it was that he couldn't sleep in after working a case in Oklahoma for the last several days.

"I'm sorry, Dean. Were you sleeping?" Rufus Turner asked sarcastically, letting himself in the room. He stooped down to Dean's ear level and shouted, "Should I come back later?"

"You know, boss, that would be swell," Dean said, hauling himself over the side of his bed to reach for the cold mug of coffee on the nightstand.

"No," Rufus replied haughtily. "It's time to rise and shine, Dean Winchester."

"What?" Dean asked, running his hands through his bed-head as if that would cure everything.

"Need you to get Kevin's stuff out of his room," Rufus replied.

"Kevin's not dead," Dean said, dismissing the order immediately. Only a Letter as high-ranking as Dean would ever be allowed to casually wave off a direct order.

"For what?" Rufus replied. "I didn't say he was dead. I said his stuff was in the way. We got a new Man of Letters coming in. You got two hours."

"What? Hell, no," Dean said defensively, taking a swig of his cold, bitter coffee. "That's Kevin's room. You're not replacing Kevin, and I'm going back to bed, so you—"

"No, you're not," Rufus pressed. "He's your new trainee. Name's Castiel Novak, graduated top of his class at Letters Academy in Sioux Falls—under Bobby Singer."

"So did Winchester, and he can't even match his socks," Meg Masters said, peeking her head around the door. She smirked before adding, "Yeah, your record still stands."

"Meg, where are you going?" Dean shouted as she jogged down the winding hallway.

"Don't worry about it," came the echoed reply.

Rufus passed Dean a manila envelope marked with the Aquarian star, and Dean knew it contained the new Letter's information. He indignantly huffed at being handed paperwork, but opened the file anyway and began to read.

Name: Castiel Novak

Age: 23

DOB: September 18, 1992

POB: Culpeper, Virginia

Status: In-Training

Dean barely glanced at the contact information, his eyes skimming for the Academy transcript. He was astounded by his findings, as the scores were right up there with his own. Sure, it had been four years since Dean was a rookie fresh out of Letter Academy, but he was still blown away by the scores so close to beating his.

"What, he's got a 970?" Dean asked incredulously. "Is he a genius or something? Uh, boss, does anybody happen to notice the new guy doesn't speak Latin?"

"Yeah, we're putting him through linguistics training now," Rufus replied. "His plane lands at 0800. Winchester, be there to pick him up."

"Okay," Dean agreed, sighing and sprawling out across his bed again.

"0800," Rufus reminded him once more as he rounded the corner.

"Yes, sir," Dean replied, reassuring him that this time, Dean would follow orders.

No wonder they wanted to put him with Dean. He was the first person in four years to make a score that high on his practical examinations, and Dean had a sneaking suspicion that Bobby himself assigned Novak to Omega.

"Benny!" Dean yelled as soon as he knew Rufus was gone. "Need you to go to the airport."

"Nah, brother," Benny said.

"It's my day off. I don't want to spend all morning in some terminal. And there's no picture, so you—," Dean explained.

"Yeah, well, you know, make a sign or something," Benny answered desperately. "What? You can't make a sign?"

"Can I? I'm going to pick up some pie," Dean said as he stripped off his undershirt and dug around in his messy drawers for another.

"How am I supposed to find this guy?" Benny asked.

"I don't know. Be a problem-solver, Benny," Dean replied sarcastically as he tugged on a flannel nearly identical to the one he took off. "Have fun."

* * *

Castiel had been on a plane for an hour, and he was already getting impatient. He expected to be working directly under Bobby Singer at the Letter Academy in Sioux Falls, but for some strange reason, his assignment changed at the last minute. Nevertheless, Castiel was sure his skills would be valued and required just as much here as in an office training new hunters.

"Exorcizamus te, omnis immundus spiritus," Castiel began, making sure his pronunciation was correct.

"Salve," a woman in the seat next to him said.

"I'm sorry, I don't actually speak Latin," Castiel explained.

"Salve," the woman repeated. "It's a Latin greeting."

"Ah, thank you," he responded, "You see, it's a job requirement. I thought I was going to Sioux Falls, and then, last minute, I'm... well, I'm headed to Lebanon."

"Oh, what do you do that requires you to memorize an exorcism?" she asked in curiosity.

Castiel didn't wait a single second to reply, "I'm a teacher, actually." He was an exceptional magician, scribe, and seer, but his true talent was hunting. Impersonating others and blending in with the civilians is what he did best.

"Really?" the woman replied.

"Yeah," Castiel affirmed.

"So's my brother," she informed him. "I'm Hannah, by the way."

"Jimmy," he replied, shaking her hand in the formality of etiquette hardwired into him after years of training.

"What school?" Hannah questioned, continuing their polite conversation.

"It's—it's a new one," Castiel said, not wanting to reveal much more information.

"Oh," she replied, nodding her head in interest.

"Yeah, it's brand-new. It—It doesn't even have a name yet." He hoped that would end her inquiries about the fictitious school.

"Excuse me, sir?" a flight attendant interrupted them. Her name tag read Rebecca. "Are you Castiel Novak?"

"Yeah," he replied, his heart racing as his alias was rendered useless.

"This message was patched to you through the cockpit phone," Rebecca explained. "Mr. Novak, wait under the baggage claim sign in Terminal C for your field training agent to arrive. Do not leave the baggage area under any circumstances."

"Thank you," he said respectfully, dismissing her with a wave of his hand.

"So..." Hannah said, breaking the silence of the awkward conversation. "You really a teacher?"

* * *

A few hours and flimsy explanations later, Castiel found himself under the baggage claim sign, perfecting his accent on the Latin exorcism. He played with a stress ball, squeezing it repeatedly as a nervous habit.

"Castiel Novak, right?" a voice called from the top of the stairs.

"Yeah," Castiel replied, raising his guard and putting a hand to his undetectable demon knife in his back pocket.

"You wanna know how I knew that?" the voice continued.

"Uh, 'cause I was told to wait underneath this sign and I am?" Castiel guessed. He took his hand off the blade as the man appeared and quickly descended the stairs to join him under the baggage claim sign.

"No," the man said with a chuckle. "Because only a guy who got a 970 on his practicals and was told to wait under a sign is still gonna be waiting there two hours later."

"Where is Dean Winchester?" Castiel asked.

"Who says I ain't Winchester?" the man said defensively.

"Well, you just said 970 like you were impressed," Castiel explained. "Dean Winchester got a higher score than I did, so from that, I would conclude that you didn't."

"I'm Lafitte," the man said, nodding his head in approval of how sharp the new recruit was. "Everybody calls me Benny."


	2. Chapter 2

**Chapter 2**

Immediately after introducing himself, Benny led Castiel to his car and headed to Omega, the Men of Letters bunker, to show him around. Despite all the wonderful things he'd been told, Castiel couldn't help but be wary of his field training officer, Dean Winchester. How could someone have a record so spotless? After all, everyone had their secrets to keep.

"Do the people around here know?" Castiel wondered aloud.

"What, that we're hunters?" Benny questioned in order to clarify.

"Yeah," Castiel said to explain what he meant.

"No," Benny replied instantly with a hardened expression. "No, We tell 'em different things. Winchester tells people he's a mechanics instructor at the local university. Harvelle says she's a trust fund kid. One girl I dated thinks I'm a learjet pilot."

"She believed that?" Castiel asked skeptically, raising his eyebrows.

"Yeah, man, you see this?" Benny said as he withdrew an object from his pocket. "Learjet key."

"Looks like a bike lock," Castiel stated upon first glance.

"You're smarter than the girl I was dating," Benny said with a laugh. The car was silent for a few moments as Castiel tried to focus on memorizing the route. As if Benny could read his mind, he added, "Don't worry, you'll learn all the backroads soon enough. Word of advice, never take the same way home twice."

"Are you often followed?" Castiel asked.

"Naw, only a few times," Benny replied. "But it always pays ta be careful."

"Hmm." Castiel pursed his lips as he noted the advice before continuing, "Tell me about Dean Winchester." He had his suspicions about why he was sent here without notice, but he hoped it was because the Academy had seen a spark in him that shouldn't be wasted in an office cubicle.

"He's the best hunter I've ever seen," Benny answered without hesitation, looking him directly in the eyes before turning back to face the road.

"That's what I've heard," Castiel replied, nodding his head in agreement. Maybe it was wrong to get his hopes up, but Castiel's excitement only escalated at the thought of training with the best hunter to graduate the Letter Academy.

Benny pulled off by the side of a seemingly empty road and said, "Well, this is it. Not bad, huh?"

"Yeah," Castiel remarked, realizing there was a large building next to where the car was pulled over. He could have sworn there were nothing but trees and underbrush there before. That only proves that even for someone with a sharp eye for witchcraft, magical enchantments could fool anyone. "Hey, why do they call it Omega?" Castiel asked, heaving his bag out of the trunk and followed Benny towards the entrance.

"This bunker has a history, brother," he began, staring at the building in front of them. "There's some of it I don't even know, but what I can tell you is this: It was once called Alpha, and it was the first Men of Letters institute in the United States. Supposed to represent a new beginnin' in a world gone topsy-turvy. Anyway, somethin' happened—somethin' big—long before I came and ever since, headquarters calls it Omega. That's about all I know."

Castiel was silent a few moments, contemplating what could have happened. Even more, he wondered why the Men of Letters would keep something important a secret. "Just be glad you're not movin' in a lot of stuff, brother," Benny remarked, drawing Castiel out of his thoughts. "Alright, so livin' here besides us, it's Sam and Dean Winchester, Jo Harvelle, Meg Masters, and Kevin Tran. Oh, and Charlie Bradbury, but she's out of town right now."

"It works, having everyone in one house?" Castiel asked as Benny turned an oddly shaped key in a hole he hadn't noticed only moments before.

"We all start to blend together after a while, you know? We're family," Benny admitted, swinging the door open slightly and closing it behind Castiel. "Oh, and if you have civilians over, they stay down here, okay? Nobody's allowed past the library without the Letter Stamp. No local girls upstairs."

Castiel took in his surroundings slowly, descending the staircase down into bunker and marveling at the sheer number of books lining the shelves. The amount of information the bunker must contain about the supernatural world amazed him. Castiel noted a pie graph on the wall made from construction paper. He stepped forward to read what was written on it.

"You know what this is?" Benny asked, pointing to the chart he was looking at.

"Looks like a chore wheel," Castiel replied hesitantly as he shouldered his bag again.  
There was a sticky note next to the graph that read: Get O.J. "Whoever's in charge of groceries is slacking," he added.

"That'd be me," he said with a grin. "Anyway, we all take turns cleanin'. Dishes, toilets, all that. For now, wherever it says Kevin, write in your name."

"Kevin's the Letter who—," Castiel began.

"Was bitten? Yeah," Benny confirmed. "Those vamps sure did a number on him..."

Castiel noticed the far-away look in his eyes, and asked, "Is he all right?"

"He's alive," Benny said with a wistful smile. "That's all we know right now. He's locked away in some safe house, but good news is he doesn't have to clean the bathrooms tomorrow. The mop is in the hall closet, brother. C'mon, I'll show you 'round," he said, motioning for Castiel to join him.

Castiel followed Benny, noting the winding path through the hall. It was going to take him a while to get used to the maze of identical passageways. Benny suddenly came to an abrupt halt, pausing at a door and glancing at Castiel. "Hey, Winchester!" Benny shouted, beating his fist three times on the door. "I got your new guy out here." He was answered by a thump on the door as something heavy was thrown against it. "Yeah, um—you'll meet him later. He's trying to sleep in today 'cause he just finished working a case last night. Let's check out your room."

They continued down the hallway until they were confronted by a woman. She had short black hair with fair skin and an annoyed expression that appeared to be permanent.

"Hey. New guy," the woman approaching them demanded. "This is Kevin Tran's room. Don't touch anything. Don't get comfortable."

"O-Okay," Castiel agreed, registering the fire in her eyes as a warning not to disregard her advice.

Castiel shifted uncomfortably as though he were under intense scrutiny—which he was, of course. "Eh, don't worry about Meg," Benny said, as she belligerently huffed and walked away.

"For real?" Castiel asked, still staring as she walked away from them. "She looks pretty intimidating to me."

Benny shrugged and added, "But maybe don't move a lot of Kevin's stuff at first."

They stopped at a door identical to the rest—Aquarian star carved in the deep brandy finished wood—and Benny escorted him in. The room wasn't particularly large, but it had ample accommodations, including a full size bed, a small dresser with a shelf for books, and a mirror and sink by the door.

"Bathroom's down the hall. I'm sure you'll find it if you really need to," Benny informed him. "Anyway, I'll give you a few minutes to unpack. Meet me outside in fifteen minutes, Novak. We're gonna pick up Sam from a job."

"Okay, I'll see you then," Castiel said as he tossed his tote on the bed and unzipped it. "Thanks, Benny." Benny nodded his head in acknowledgement as he left the room.

* * *

Sam wasn't in the mood to be interrupted today. He had been running on coffee since three in the morning, and that was only the beginning of his troubles. Every time he caught a glimpse of the shapeshifter on a security camera, it would change form. This shifter was strong, fast, and eager to kill. What Sam couldn't understand is why his phone wasn't buzzing every few hours with another body being found.

He knew he would function better with a couple hours of sleep, but Sam just couldn't bring himself to give up yet. There had to be some lead he could follow to start the hunt, but with a shifter that knew how to pristinely get away with murder, it was a difficult task to find one. One thing was for sure, Sam would forego sleep indefinitely until the job was done.

He was so focused that he hardly noticed his motel room door's lock being picked. When Sam detected the noise, his first instinct was to reach for the handgun by his side, aiming it directly for the door's opening.

"Hey, Sam!" Benny's voice greeted as the door swung open, not even flinching at Sam's characteristic precaution. He instantly lowered his weapon and stowed it away after he realized it was only Benny. "This here is Castiel Novak, Man of Letters. He's takin' Kevin's room."

"You're a Winchester," Castiel noted, extending his hand. "Any relation to Dean Winchester?"

"Yeah, that's my brother," Sam replied, barely glancing up from his laptop to give Castiel a decent handshake.

"Benny told me that you were working on a shifter operation," Castiel said. "I didn't realize that was such a problem here in Kansas."

"It is," Sam answered dejectedly. "At least ten per year within a hundred mile radius of the bunker. And this one has me chasing him in circles."

"Yeah, ya gotta watch out for shapeshifters. Don't want anybody stealin' your skin, do ya, Sam?" Benny asked in an attempt to lighten the mood.

"Yeah, one alone can take over a town," Sam answered quickly. "As it turns out, this one has been popping up at a Gas N Sip once every three hours since yesterday."

"How do you know it's same shifter?" Castiel inquired. "Is it not common to have more than one in the same area?"

Sam eyes instantly darted to Castiel as though he'd had a sudden realization. "That's brilliant," he said as he reverted his attention back to the screen and began to type feverishly. "I know the connection between the vics is they're all part of local government. It doesn't make any sense for one shifter to go after these people, but if it's a team, they're impersonating the officials to get inside the town."

Sam quickly combed through the recent local articles on his seemingly endless database and found one new addition—an article about a school board member being found dead in the alley behind a pizzeria. "Jackpot. I've been looking for a lead since early this morning. Benny, where'd you get this guy? He's a genius."

"I know he's sharp, Sam, but maybe he's just better rested than you," Benny said, giving Sam a once over. "Come home. Get some shut eye. A couple hours should do the trick."

Sam took a deep breath, looking over all the evidence he had found. It was hard to give up on something he'd spent so many hours trying to finish, but he knew going back to Omega with Benny was the right thing to do. "Okay," he decided, slowly closing the lid to his laptop and gathering the papers randomly strewn across the table. "I'm only supposed to have this room until tonight anyway."

* * *

When they arrived back at the bunker and showed Castiel where the parking garage was located, Sam stumbled up the stairs into the main hallway, mumbling something to the effect of, "I'm going to bed. See you later."

"Okay, Novak, it's lunchtime," Benny said, glancing at his watch. "You wanna make a salad? A sandwich? We've got just about everything 'cept orange juice. I'm not slackin' that bad."

"Yeah, sure," Castiel replied. "Where's the kitchen in this place?"

"That way," Benny answered, pointing down the hall. "Third door on the right. C'mon, I'll show ya."

Benny led him down the hall to the kitchen. As they rounded the corner into the doorway, Castiel saw a familiar-looking man rummaging through the shelves. The man was tall in stature with a five o'clock shadow and a serious case of bed head. It took him a few moments to place the man, but Castiel knew why he seemed so familiar. After all, he had spent the last few years at a school that practically worshipped the man's talent for hunting. "What's up? You must be Novak," Dean said when he noticed Castiel.

"Yes, sir," Castiel replied, standing up straighter. "You're Dean Winchester."

Castiel had only seen a photograph of Dean receiving an award for Letter of the Year. This Dean Winchester was a stark contrast to the clean-shaven guy wearing a monkey suit with a plastered on smile.

"Mmhmm," Dean grumbled, searching the cabinets and pantries for something to snack on.

"I'm honored to be training with you," Castiel said, still standing about face with an awestruck expression.

Dean shrugged off the attention and opened the refrigerator to scrounge through its contents. "Excellent," he replied.

"Oh, I'm ready to begin, sir," Castiel said with enthusiasm.

"Now?" Dean asked skeptically, looking up in a quizzical air.

"Yes," Castiel replied.

"Good attitude, Novak," Dean commented, turning back to the fridge and resigning himself to warming up a leftover pastrami sandwich. "Um, you familiar with the chore wheel?"

"Yes, sir," Castiel replied, watching as Dean set the toaster oven to the highest temperature and shoved the sandwich in.

"Okay," Dean began with a smile, turning to address Castiel. "To get you started, wherever it says 'Dean', I want you to substitute 'Cas'—can I call you Cas?"

"Of course," he answered.

"It'll help you with the whole undercover name association thing," Dean assured him. "So tonight, where it says 'Dishes - Dean', I want you to think—"

"Dishes - Castiel," he finished as the toaster oven dinged beside him.

"970 on your practicals," Dean said with a grin, taking a bite out of his pastrami sandwich.

"Yeah," Castiel replied. He had expected someone more professional than this. The way they spoke of him at the Letter Academy made it sound as if the one and only Dean Winchester could do no wrong. He was what every new initiate strived to be, and for him to be so casual and human seemed unreal for Castiel.

"Think of it as a whole wax on, wax off sort of thing," Dean said vaguely as he started for the door. "Now if you gentlemen will excuse me, I'm off in pursuit of the perfect bottle of whiskey."

"That's Dean Winchester?" Castiel asked incredulously.

"That's Winchester, alright," Benny chortled to himself. "Okay, let's find something to eat."

* * *

Meg sifted through the Men of Letters files, searching for more information on known vampire nests in the area. Kevin was attacked on a hunt almost a week ago, and she was trying to bring those at fault to justice. The phone rang from across the room, and she hesitantly decided to get up and answer it.

"Who's this?" Meg asked heatedly. No one was except headquarters and the Men of Letters at Omega were supposed to know the phone number, so on the rare occasion the phone rang, it was safe to assume it was important.

"Who do you think it is?" Kevin Tran replied.

"Kevin," Meg said in surprise, taking the phone from its hook and bringing it back to the table she was using.

"It's a safe house. It's safe, boring as hell," Kevin said with a scoff. "Got a gun loaded with silver bullets and nothing to do. Those vamps still want me dead?"

"Uh, they're on radio silence, but you gotta figure...," Meg started.

Almost a week ago, the Men of Letters were tracking a nest of vampires that were pillaging for victims on the other side of town at a bar. Kevin was sent to investigate, but he was severely battered and bruised after a confrontation with the vampires, in which they figured out he was there to hunt and kill them. What they didn't know was that Meg was watching them from across the bar as Kevin's backup, and when they began to attack Kevin, she charged at them and the two vampires ended up with their heads severed from their body. Since then, Omega hadn't received any alerts from the local police about activity around the bar, but Meg knew the nest was still there and ready to avenge those she beheaded.

"They want you dead, too?" Kevin asked.

"Yeah," she replied quietly. The line was silent for several seconds. "Anyway, the guys are at the park—football, frisbee, that kind of thing."

"Hmm, so you give away my room yet?" Kevin questioned jokingly.

She paused, taking a deep breath before answering, "It's not a done deal."

"What! They gave away my room?" he asked. "That's cold. It's not like I'm dead."

"I told him not to touch your stuff," Meg said helpfully. "Anyway, it's not Omega without you. Get your strength back. Watch some crappy soap operas while you still have free time."

"Yeah," Kevin agreed, scoffing at Meg's attempt at a joke. "I'll talk to you later, Meg. I'll come home soon."

* * *

"Come on, boy, drop it," Castiel pleaded with a mangy dog. After lunch, Benny decided to show him around town, and because it wasn't a busy day, Jo and Dean joined them in a visit to a local park. "Hey, I just bought that. Hey! I'm not in the mood for this," he grumbled as the dog scampered away with his newly bought frisbee.

"Oh! Enjoying yourself?" Jo asked, sitting down on the ground and motioning for Castiel to join her.

"No, I'm not," he admitted, sitting next to her on the ground.

"Look at him," Jo said, pointing at Dean tossing a football back and forth with Benny.

"You know, in Letters training, they talk about him like he's a god," Castiel said with disbelief. "I mean, he had more solved cases in his first year than his whole class combined."

"So you were expecting somebody a little more formal, suit and tie-ish?" Jo asked.

"Yeah, something like that," Castiel agreed.

"He was like that once," Jo admitted. "Don't get me wrong, his father raised him as a hunter, so he's always been pretty scrappy. But a few years ago, something went down. He took a leave of absence, came back all zenned out like that."

"You don't know what happened?" Castiel asked.

"Nope," she replied. "He never talks about it."

"You're not curious?" Castiel questioned. "Maybe he's just crazy."

"You're right, he is a little crazy," Jo agreed with a laugh. "The house is a tight fit, though. You're gonna find out real fast there are no secrets in Omega—we're family and we don't lie to each other."

"No secrets," Castiel mused. "Except for Dean Winchester."

"Yeah," Jo replied thoughtfully. "Except for Winchester."

* * *

"Hey, Dean!" Meg shouted as they arrived in the bunker. "You got a message from a guy named Azazel!"

"You checking my messages now?" Dean asked defensively, snatching the phone away from her as soon as he saw it in her hands.

"Yeah, but I don't think it's him," Meg replied doubtfully. "He sounded pretty confused. Maybe it's his meatsuit? Demons have been known to give over control for a few minutes."

"Yeah, uh, he's off our active list, Meg. Besides, Azazel probably just smoked out and left the vessel. A little post-traumatic, but he should be fine on his own," Dean scolded her. "Seriously, are you checking my messages now?"

"I know him," Meg replied darkly. "He works for Lucifer."

"Works for?" Dean asked lightheartedly. "He probably does their decorating downstairs."

"He works for Lucifer," she repeated, stressing her words. "This could be our chance to get intel on him."

Dean sighed, realizing he wasn't going to win an argument with Meg when she was this determined. "He was a low-level demon, Meg," Dean explained weakly. "We've wired him before when we actually knew who he was possessing, and he dropped a few names. That's it."

"Come on, Winchester," she grumbled.

He debated over the two options. He could go with Meg's plan to sure there were no demons around this guy and potentially exorcise Azazel... Or he could let a demon go unchecked and potentially get others killed. Definitely option one. "Okay, fine," he agreed. "Cas, how'd you like to get your feet wet this morning?" Dean asked.

"What?" Castiel inquired in confusion.

"Congratulations, Cas," Dean said sarcastically. "First day on the job and you get the chance to bust a demon."

"What do ya say, boss?" Benny asked. "Call in to Sioux Falls?"

"No, no," Dean waved him away dismissively. "It's always better to beg forgiveness than to ask permission. You know that, Benny." Dean flipped the phone open and listened to the short message. There wasn't any detail to go on other than the location of the vessel. "You're right, Meg. He sounds pretty dazed and confused."

He dialed the last called number, and everyone gathered around him, close enough to hear the call. "Got your message, man," he said as soon as the call was answered. "What's up?"

"Hey," the gravelly voice carried through the receiver. "Your number was the last one on my call list, but I don't remember anything that's happened in the last few weeks. I went to my house this morning, but my wife was terrified... wouldn't even let the kids outside to see me."

"Man," Dean said doubtfully, feigning sympathy for the man. "You really want to know what happened?"

"You can help me?" he asked cautiously.

Dean pretended to weigh the question for a moment before replying, "Yeah, I got somebody who can come by and give you the rundown. Your place, one hour." The phone beeped as Dean ended the call.

"Are you really gonna tell him he was possessed by a demon?" Castiel asked, confusion laced in his voice.

"Absolutely not," Dean replied. "I'm going to send you in to scope the place for demons. If it turns out to be nothing, we'll go undercover as pest control—ward the rugs, and give him an excuse to line the windows and doors with salt for a while, just in case."

"Where we setting up?" Benny asked.

"Put a van on the end of the street to scope the place out," Jo answered. "Send Cas in wired with some of Charlie's gear."

"Yeah, should be good," Dean replied. "If it turns out to be him, we'll trap and exorcise him while we're there. Until we know for sure...," he paused hesitantly, letting everyone internally finish his sentence. If they weren't certain there was a possession, they were never allowed to give away the Men of Letter secret. Rule number one: When posing as civilians, there was no such thing as a supernatural world. "Alright, Novak, let's see what you're made of," he said with confidence.

* * *

 **A/N: A big thank you to my beta reader, Skipper96, for helping me round out this chapter! XD Also, reviews are greatly appreciated. I love hearing feedback from others, and I always smile to myself when I get something from you lovely folks in my inbox.**


	3. Chapter 3

**Chapter 3**

Dean slid into the driver's seat his beloved Impala and pulled the creaky door shut. He motioned for Benny to take the passenger seat as Castiel hesitantly crawled into the back. Dean turned the key and heard the engine crank. The speakers roared to life with the sound of an electric guitar riff.

"Ah, Ted Nugent," Dean sighed, putting the car in reverse and backing out of the bunker's garage. "Stranglehold always calms my nerves. What's the matter, Cas?" he asked, noticing his tense expression in the rearview mirror.

"Sorry, I'm just not partial to the sound of rock music," Castiel replied. "I don't know why, it just sets my teeth on edge."

"S'okay," Benny said, changing Dean's cassette tape out and going through the collection in his dash. "What d'you say, Dean?" he asked, holding up a tape with a barely legible scrawl.

"Whatever," Dean answered. "You can play the Bristol Sessions all you want, but nothing beats Zeppelin in my book."

"Yeah, yeah," Benny replied as he put away the cassettes. "Hey, Jo's driving, right?"

"She's bringing Sam and Meg over to headquarters with us," Dean replied. "I swear, we need a van or something to get all of us from A to B."

As soon as Benny inserted the new cassette tape, Castiel felt his muscles uncoil and his breathing even out. "So... what exactly am I getting myself into?" Castiel asked, fidgeting with his wristwatch in the absence of his stress ball.

"Alright, Novak," Dean began, glancing at him in the rearview mirror. "This is gonna be a simple, okay? You're gonna walk in, and you're gonna make small talk. If he's possessed, you'll know by his reaction to holy water. I don't care how you do it—subtle or a splash in the face—just get it done. After that, you're gonna give us the signal whether to move in or not."

"Okay," Castiel answered with a nod of his head. He pulled out a small notepad and stub of a pencil to take down the information. For kinesthetic learners like himself, transcribing made learning a bit easier. "What's my name?"

"Uh, your name is Cas," Dean replied nonchalantly, drumming his fingers against the steering wheel to the rhythm of the song.

"Right," Castiel answered, pausing for moment before asking, "A last name?"

"Don't give him a last name, Cas," Dean instructed.

Castiel continued jotting down notes in his pad, scratching until Dean reached in the back seat to snatch it away, throwing the notes out the Impala's window as they were speeding down the highway. "Hey, why—why did you do that?" Castiel asked.

"Because you can't take a cheat-sheet with you, okay?" Dean replied simply. "Trust me, just keep it simple. People won't ask a lot of questions if they don't want you asking questions either. You feel me?"

"How do you and I know each other if he asks?" Castiel questioned further.

"If he asks, just say 'around'," Dean said. He didn't want this to be complicated. It was supposed to be a confidence-building first case for his trainee to help him get experience.

"We can make it a little interestin'," Benny said, a wide smile creeping across his face. "Put him in the show."

"No way," Dean replied.

"Why not?" Benny asked.

"That contradicts everything I just said, Benny," Dean explained.

"Um, what show?" Castiel asked in confusion.

"Alright, look," Benny continued, turning to face Castiel. "There were a few leviathans a while back, and these guys are hard-core evil. Type of guys that'll eat you jus' to keep from gettin' hungry."

"In the middle of this thing, I get some stupid award from headquarters," Dean added with a roll of his eyes. Since Castiel had met him, he'd realized Dean had a characteristic streak of insubordinance. That was unexpected, considering the honors they gave him at the Academy and Castiel's preference for following the rules. "Letter of the Year, and in their infinite wisdom, they send a camera crew. So for about a week, I've got my face plastered all over the place next to an Aquarian star."

"Not good," Castiel commented.

"Not good at all," Dean agreed. "Now, we're meeting with some of the top guys in the family. They know they've seen my face, but they can't place it. Now they're getting spooked."

"Award coverage?" Castiel guessed.

"Tell 'em whatcha said, Dean," Benny said with a chortle.

"I could tell it was going down fast, so I told them it's true," Dean explained. "You got me. I don't brag about it, but I'm an actor. Sometimes I play a hunter on television."

"They believed that?" Castiel asked incredulously.

"Hell no!" Dean replied with a laugh. "So now we got gun barrels jammed under our chins and they're about to start chowing down, right? And I just start talking out of my ass. I'm sure you've seen the commercial. It's a show about two brothers who drive around the country catching oddball cases, eating crappy diner food and hunting evil."

"Really?" Castiel asked in surprise. "And they believed that?"

"No, no," Dean assured him. "Straight up, man."

"You told them you were a hunter?" Castiel asked, still in shock that anyone could be that reckless and intelligent at the same time.

"No, my friend," Dean clarified. "I told them my character was a hunter. Never said it was great show. Fake blood spatter, daddy issues, alcoholism."

"Told 'em I play a vamp, myself," Benny said, looking very proud of himself. "So Winchester did the craziest thing. They're not buyin' any of this. Tell 'em what you did."

"Well, basically, I knew we're screwed if they search us, so I pull out my demon blade and toss it on the bed," Dean admitted.

"Prop from the show," Castiel assumed. "And?"

"And they're looking at it, you know, real close," Dean continued, trying not to smirk. "And this idiot tells me it looks like something that came out of cracker-jack box."

"It's a real low-budget show," Benny said seriously, trying to mask his amusement.

"Yeah, right," Castiel said.

"To this day, one of them levis still has an autographed picture of Dean Winchester hangin' in his cell," Benny added.

"Wait, what? You kept him alive? How did you get out in the first place?" Castiel asked.

"Yeah, we nailed 'em all but one, didn't we Benny?" Dean said with a laugh. "Anyway, Sam got in and gave a few of them the borax treatment. That gave us enough time to get free and bust some heads. There was just one left... We got him in a sort of monster prison zoo. If a Letter thinks a monster knows enough to be useful, he's held captive until he talks."

"Really?" Castiel asked *,eyes widening in surprise*

"Yeah, there's a lot they don't tell you at the Academy," Dean admitted. He paused, and Castiel wondered if Dean would tell him the entire truth about the secrets of the Academy. At the same time, Castiel couldn't help but wonder if Dean was a part of those secrets. After a few uncomfortable seconds had passed, Dean added, "But don't worry, Cas, you'll catch on."

"Yeah," Benny continued, breaking into their conversation. "Ya see, headquarters is right up here on the left. It's hidden from the city 'cause ever'one thinks it's an insurance company."

"Oh," Castiel said in surprise. "So does anyone actually have insurance with you guys, or—"

"Naw," Benny replied. "Course not, but it's just to keep up appearances. Rule number one, Cas. Rule number one."

The Impala slowed to a halt at the curb, giving Castiel the chance to observe the building. If he had been a civilian in this town, he'd have thought it was a run-down business, destined to be demolished in the near future to build a new grocery store. But Castiel wasn't born to be an ordinary civilian. His mind was too sharp and inquiring to be shielded from the truth.

From the outside, this building looked far from decrepit. The Men of Letters were sticklers for maintaining appearances, and it showed in their work. The lawn was well-kept, and sidewalk was swept. Even the azalea bushes were neatly trimmed. Of course, this wasn't due to physical labor. It must be magical charms that kept this place looking spotless because the grass was too freshly mown to not have a mix of leaves and clippings strewn about.

The three of them climbed out of the Impala and walked up the sidewalk to the front door. When they entered, Castiel was surprised to find it looked like a regular business. There was a receptionist at the front desk, and several offices in the back. Castiel was hesitant to follow, but Dean and Benny seemed to know exactly where they were going. They led him to one of the office spaces on the right side of the building.

"Who was that?" Castiel asked.

"Oh, that's just Krissy," Dean said with a shrug. "She knows about what we do, but she keeps our secret. You see, her father was a Man of Letters, but he was killed by a vampire when she was a teenager. So as soon as she was of age, we hired her as a receptionist."

"So... what does she do if this place isn't really an insurance company?" Castiel asked.

"We get tourists in here sometimes, asking for directions back to the interstate," Dean answered. "The locals will stop to use the restroom or ask for information on our services. Krissy takes care of all that. Not to mention, she took all of our files at Omega and made them digital."

"She couldn't have done it without Charlie," Jo added as she entered the room, followed by Sam and Meg. She took a seat behind the desk and asked, "Were you racing us?"

"No!" Dean replied, defensively crossing his arms. Jo raised her eyebrows. "Maybe," he admitted. "I totally beat you."

"Okay, you two," Sam interrupted. "Stop flirting and get some work done."

Dean smirked as Jo narrowed her eyes. "Alright, Cas, I need you to put this on," she said, handing him an earwig and a few other wireless gadgets that Castiel couldn't identify.

"How do I do this?" Castiel asked, looking down at the technology in his hands and squinting.

"Charlie's magic," Dean informed him, loosening Castiel's tie and attaching the transmitter. "Sends everything to us."

From behind, Dean heard someone clearing their throat to catch his attention. Dean turned to find Rufus Turner standing behind him with an exasperated look on his face.

"So I'm in the middle of breakfast this morning, and I get a call from Sioux Falls," Rufus started. "They were asking why they haven't been informed that we're moving in on a demon bust. Imagine my surprise since I didn't know we had a demon vessel in the area."

"We don't," Dean admitted, scratching his bristly cheek. "Pulled him off the list a month ago."

"And we're doing this why?" Rufus asked, his eyebrows raised in skepticism.

"That would be Meg's idea," he replied with exasperation. Dean faced Castiel and waved his hand back at Rufus.

"Castiel Novak, this is Rufus Turner."

"I'm your resource officer," Rufus informed him.

"Oh, it's a pleasure, sir," Castiel said formally, extending his hand.

"Let me know how long that lasts," Rufus said sarcastically as they shook hands. "Winchester taught you everything he knows yet?"

"Yes, sir," Castiel replied, glancing over at Dean. "Wax on, wax off."

"I assume that's an inside joke," Rufus said dryly. "I don't like inside jokes."

"Understood, sir," Castiel responded.

"Okay, Cas," Dean began. "This guy has a family loyalty, so he's not likely to rip you unless Azazel takes over again. He's got his wife and kids that think he's crazy already, so he's not likely to start shooting. This should be easy."

"Yeah, it should be," Castiel agreed, taking a deep breath and adjusting his watch.

"Now, this isn't his actual home. It's more of a safe house that belongs to his sister," Dean said. "So if it looks like he's a doomsday prepper, he probably is. Are you nervous?"

"Yes, sir," Castiel answered.

"That's good," Dean said with an encouraging slap on the back. "Don't get shot, Cas. Let's do this right."

Castiel took a shuddering breath to calm himself, and casually knocked on the door, reassuring himself that confidence was key and this was the first step in working his way to the top. Slow and steady wins the race. Castiel heard the bolt click and the door squeak open, and he steeled his nerves to face the man.

The man opened the door enough to peek his head out to examine Castiel. "Dean's friend?" he asked suspiciously.

"Cas, actually," Castiel responded, spreading his arms wide open in a careless and confident manner.

"Yeah, come on inside," he said, pulling the door back and stepping aside. "I'm Ned, by the way."

"Thanks, Ned," Castiel said. The door shut behind him, and Ned quickly bolted and locked it as though he were paranoid.

"So you and Dean are friends, huh?" Ned asked, gesturing for Castiel to sit on the reclining chair adjacent to him.

"Yeah, I met him, you know, around," Castiel replied vaguely*, waving his hand in the air dismissively and*, accepting the invitation to sit.

"Yeah? Around?" Ned questioned, probing him for further information.

"Well, I'm his guardian angel," Castiel supplied, trying to keep his composure. "I pulled him out of hell," he added. Castiel mentally facepalmed himself as he realized this man wasn't aware of their cover story. Castiel had hoped that conversation would clear things up, but babbling just seemed to complicate matters even further.

He could just imagine Dean back at headquarters muttering to himself about what an idiot Castiel was for letting on this much. Then again, he could picture Dean jokingly commenting, "Twenty bucks says he shows him the knife," too.

"In a television show," Castiel explained quickly. "I play his guardian angel in a low-budget television show."

"I was gonna say...," Ned remarked. "My friends are messed up. But yours are crazy!"

"Yeah, of course," Castiel said, trying to shake off his rocky start and build a trust with this man.

"So... Here's the problem, man," Ned began. "You know how things, they get stacked up? You just can't seem to sleep at night. You keep having all these nightmares—almost like they're memories—but you can't remember doing any of it."

It appeared to Castiel that they had wasted an afternoon chasing an ex-vessel that was suffering from memory loss and clinical depression. A sad situation for the vessel, but nevertheless, a waste of time for the Men of Letters.

"What are we talking about here?" Castiel asked, wanting to be certain the man was not possessed before he was done.

"Man, I don't know," Ned said with an exhausted sigh. "You want something to drink?"

"Yes, please," Castiel answered. This would be the perfect time to give him the holy water test and be sure he was clean. After that, Castiel could make up some excuse to get out of here as soon as possible.

"Alright, I've got some water in here," Ned said, standing to retrieve two glasses of water from the kitchen.

"Thanks," Castiel replied as he was handed a tall glass of water.

He took out the holy water from his pocket—disguised as a flask of liquor—and doused some in the glass.

"You got a taste for the watered-down stuff, huh?" Ned asked, noticing Castiel adding something to the glass.

"Can't say I blame you. Never cared for anything so strong."

"You want some?" Castiel offered nonchalantly.

Ned paused hesitantly, waiting a moment before replying, "No, I'd better not."

"You sure?" Castiel pressed, wiggling the flask in a tantalizing way. "It would ease your nerves."

"No, I'm sure," Ned said with more confidence than before. "But... I do have something you may want to see out back. If you don't mind continuing our little conversation someplace else. I don't exactly feel safe squatting in this dump."

"Okay," Castiel agreed, politely taking a sip of his water before standing to follow Ned.

"Excellent," the man replied, angling himself just enough so Castiel wouldn't see his eyes flicker yellow.

"Come on!" Sam exclaimed in frustration, slamming his hand down on the table. "You told him not to change locations, right?"

"No, I didn't," Dean muttered. He ran his hands through his hair and took a deep breath. "Damn it! I need somebody out in that alley right now."

"I can't help from here, but if we can get Benny in there on foot, I could get you a visual," Sam replied, urgently analyzing his computer screen.

"Do it," Dean ordered as he threw Benny the keys to the Impala. "We can't lose him on his first day."

Benny caught the keys from across the room and took off out the door. He knew it was an emergency because otherwise Dean would never let him drive the Impala. Benny turned the ignition and stamped his foot on the gas, tearing off down the street. From the time it took Castiel to get there, it should only take him ten minutes to speed across town.

It was important to get a visual—not so much for Castiel's safety as it was for the team's. Cameras could see things the naked eye could not, and even with their skill and knowledge, they could be fooled by a demon, a shapeshifter, or any other supernatural being.

Benny contemplated whether this demon vessel was actually empty or not. Surely, the camera would have caught his eyes flare. But there was no way to tell unless Castiel had managed to give him holy water.

When he finally arrived at the vessel's home, Benny quickly moved to follow Castiel around the back of the house. He stayed quietly at the side, just out of sight so as to eavesdrop on their conversation.

"So... what do you think?" the man asked. "It's a pretty good deal, right?"

"Yeah," Castiel agreed. "It sounds great."

Benny knew that could only mean one thing... Castiel was on the verge of making a deal with a demon. He rounded the corner and withdrew his gun. "Azazel!" Benny shouted, taking the attention off of Castiel. "Stop, or I'll shoot!"

"Oh, please," Azazel said as he turned to reveal his yellow eyes. "You don't want to shoot this innocent man. It's all nice and comfy in here. You know, he's a screamer. Not a quiet moment since I've been in here."

Castiel snapped out of the stupor Azazel had put him in. He'd almost convinced him to sell his soul. The only comfort was that the deal was never made. As long as Castiel had trained for this moment, he didn't know what to do. Benny pulled a gun on him, so if all else failed, he could always shoot. But then, Castiel remembered why he became a Man of Letters. It wasn't just about killing evil. It was about saving people and hunting things, making sure people went home to their families safely.

Before he knew what was happening, Castiel had the demon by the arm, retrieving the demonic handcuffs from his pocket and slapping them on Azazel's wrists.

"If it goes the way I plan," Castiel started, emptying his flask of holy water on him. "He won't ever need to shoot."

Benny lowered his weapon and began to recite, "Exorcizamus te, omnis immundus spiritus, omnis satanica potestas—"

Castiel took a deep breath, feeling the demon shake with pain as it was expelled from the vessel. The man collapsed to the ground, and Castiel removed the handcuffs.

"That was one hell of a move you just pulled, brother," Benny remarked. "You've gotta understand... Ol' Yella Eyes wasn't your ever'day demon. The holy water weakened him. That's why the exorcism worked. You did good, Cas. Real good."

When they arrived at Omega, Dean decided getting Castiel back safely was a cause for celebration. Of course, Dean's idea of celebration was getting drunk, and he would usually find any excuse to do so, but that was beside the point. Everyone was relieved Benny and Castiel exorcised a demon made it out in one piece.

"Hey, Cas! Get this," Jo began. "Sam and Dean were undercover with this vetala gang. Sam figures if Dean can do it, he can too."

"Damn straight," Sam replied, taking a swig of his beer.

"So he tells them that he plays this tough-guy killer," she continued.

Dean continued, "Yeah, the guy he shot was sitting on the toilet. He tells them I shoot this dude when I catch him reading my dirty mags on the john. Mmhmm, two slugs. One in the arm, one right in the chest."

"Couldn't even make me a good shot, could you?" Sam asked to the amusement of everyone else.

"Hey!" Benny called as he entered the room. "What are we celebration'?"

"What's up, man?" Dean asked. Benny had graciously stayed behind to write up the paperwork to be sent to Sioux Falls tomorrow morning.

"Bad news," Benny informed him. "Demons have got the guy Azazel was possessin'. At this point, they've gotta have his family as leverage, too. He panicked when they asked him about Cas...," Benny continued. "Said he was his brother-in-law."

"He said what?" Castiel asked incredulously, trying to keep his voice from shouting *from raising his voice*

"Yeah...," Benny confirmed. "But we got lucky. He does have a brother-in-law with a passin' resemblance to Cas.

By which I mean he's white with dark hair. We gotta do something about your height. He's gotta scar above his left eye, and if it comes up, you've lost a hell of a lotta weight. Other than that, he's a perfect match."

"One minute," Rufus said, holding up his hand and gesturing for Castiel to follow him. He stepped outside the room to meet with Rufus in private. "So how's your new job so far, huh?" Rufus asked.

"Oh, well, it's great," Castiel answered. "Cleaned some dishes, learned the difference between pie and cake. What exactly is gonna happen here?"

"Kidnapping a family is messy, Castiel," Rufus began. Castiel looked into his eyes and could tell Rufus knew all too well how awful a kidnap could get.

"Alright, they're bailing you out because they want assurance that he won't talk. They think that you're family. They get you to do something illegal. Then if he talks to us, they turn you in."

"Illegal?" Castiel repeated.

"Yeah, it's predictable," Rufus explained. "They're gonna ask you to kill someone, Castiel. Now all you gotta do is get a name, okay? You come back to us, that's it. We have this guy, Ash, who works at the paper. He'll play ball with a homicide story and an obituary. They think the guy's dead, they let the family go. You don't have to do this."

"Yeah, but if I don't, what happens to that family?" Castiel asked. He wanted nothing more than to say no—but Castiel knew that wasn't the reason he was sent to Lebanon.

"Alright," Rufus said, opening the door in consent of Castiel's decision.

"We've gotta assume these pricks have the same intel we do," Dean said. Castiel could tell he was the authority in the room because he was the only one standing. "You've got exactly one hour to become this guy. Your name's Emmanuel Allen. Got it, Cas?"

"Emmanuel Allen," Castiel repeated. "Yeah."

"Your wife's name is Daphne," Dean continued, reading from a sheet of information on him. "She is Ned's wife's sister. Her name is Catherine."

"Wait, wait," Castiel said. "My wife is Daphne or Ned's?"

"Yours," Dean said patiently. "Write it down."

"Sure," Castiel responded, grabbing a pencil and paper to write down his notes.

"You ever been to Nashville?" Dean asked.

"I drove there once in college," Castiel answered.

"Alright, well, now you're from there," Dean said. "Don't worry, not everyone sounds like Benny there."

Almost an hour later, Dean had taught him everything there was to know about becoming another person. He drilled Castiel on specifics, asking questions about Emmanuel only he should know.

"Your arrest in '04?" Dean fired.

"I boosted a firebird," Castiel answered without hesitation.

"Nice," Dean commented before continuing to drill him. "Wife?"

"Daphne," he replied. "She's a year younger than me."

"What's your name?" Dean asked. "Cas?"

"Uh...," Castiel paused, waiting as the answer came to him.

"What's your name?" Dean pressed, knowing Castiel was sharp enough to remember.

"Allen. Emmanuel Allen," Castiel exclaimed as he remembered. "Damn it! I know that. I know that."

"Whoa, whoa, whoa," Sam interrupted as he entered the room. "Wait a second. January of this year, suspicion of demonic possession. After the demon was exorcised and he got the anti-possession tattoo, he was noted by a Men of Letters group in Memphis to be addicted to their blood."

"This guy's a junkie?" Dean asked. "When's the last time he could've gotten a fix?"

"Uh, a few days ago?" Sam guessed.

"Okay, Cas, you're going to have a little more of a challenge than we thought. You're in withdrawal from demon blood, so you're gonna be shaky," Dean informed him. "See? You're a natural."

"Alright, so I got a pair of boots with lifts and a wallet for an Emmanuel Allen. It's got the plastic, money, I.D., whatever. No, no, no. This thing is brand-new. Benny, go mess around with it outside or something," Dean instructed, tossing the wallet in Benny's direction. "Alright, Emmanuel Allen, this is your transmitter, okay? Now we can hear you, but you can't hear us. Very important. If they sweep you, press this button. Cuts the transmission. Push it again to restart. You got it?" he asked.

"Yeah," Castiel said with shaky confidence. "You're tracking me, right?"

"The GPS signal's too hard to cloak," Sam informed him. "But we've got your audio. Just give us as much info about your twenty as you can without tipping him off. You'll be all right."

"Whoa, Benny, let me see that!" Dean exclaimed as he saw the tattered state of the wallet.

"C'mon," Benny said as he tossed it to Dean. "It doesn't look that bad."

"Guy carries this in his pocket. He doesn't drag it behind his car," Dean remarked as he thoroughly examined it.

"It's gettin' dark out there, brother," Benny said defensively. "What you want?"

"Perfection," Dean retorted as he turned to hand the wallet to Castiel. "What's your name, man?"

"Emmanuel Allen," Castiel replied without hesitation.

"Then what are we waiting for?" Dean asked. "Let's do this, Cas."

* * *

 **A/N: Thanks for reading! I hope you enjoyed. And as always, reviews are appreciated.**


	4. Chapter 4

**Chapter 4**

Castiel was anxious, dreading what was to come as he trudged through the entrance of the whorehouse. His fingers ached for the stress ball that usually eased his tension, and twisting his watch was also impossible because Dean had been sure to remove it before he left.

Now he found himself in a shady neighborhood—in a brothel, of all places—trying to weave through the crowd. Castiel had never been to a house of iniquity before so he didn't know where to look for a hidden office, but it seemed the two muscle-bound men sitting by the door with their arms crossed were some sort of security for the business. That was as good of a place to start as any. He sauntered across the room, dodging a few couples intensely focused on each other.

"Allen, Emmanuel," Castiel introduced himself with an arrogant smirk. If he was going to do this, he might as well do it with some confidence.

The man unfolded his arms to procure a clipboard from underneath his chair. Almost as if they were waiting on him. "Sign," the man said unenthusiastically, passing him the document. Castiel picked up the pen and quickly gave a signature for his alias. "Mr. Allen, raise your arms, please," the other man said as he stood to his full height.

Even at six feet tall, Castiel felt small in this man's presence. He did as he was told. Castiel had never had a problem with invading personal space, but this man crossed the line more than usual. Castiel shrugged it off as thoroughly inspecting for hidden weapons, but he raised his eyebrows more than a few times at the man's lack of boundaries.

"You may see the boss, now," the man intoned gruffly, leading him to the back of the building. "He's been waiting for you."

"Oh, really?" Castiel asked sarcastically as he swaggered behind him. "Just what does he think I can do for him?"

"You'll see," he replied as he opened a fire exit door.

Castiel expected a flash of light and an alarm signaling to evacuate the building, but when the fire exit opened, Castiel realized it didn't lead to a back alley or a parking lot. It seemed as if the room were an old-fashioned study—books lining the shelves, an untidy desk, and an alcohol collection. Still, Castiel sensed he shouldn't trust the man sitting behind the desk, grinning maliciously. At this point, he wouldn't be surprised if the man was possessed.

He jumped unexpectedly as the false fire exit door slammed behind him. "It's a damn miracle code enforcement hasn't nailed your ass," Castiel commented as he took a seat across from the man.

"You listen here, sonny," the man said as he leaned forward slightly. The calmness in his voice made it that much more petrifying, but Castiel was determined to follow through with his mission. "We are not here to discuss the safety of humans, and if I hear one more snide remark out of you, I will personally gut your family while you watch. You feel me?"

Castiel nodded slowly, reluctant to agree with someone who refers to everyone else as "humans" as if he weren't one. It seemed Castiel was correct in his assumption that this man was possessed. "Good," the demon replied as he sat back on his haunches, intensity disappearing from his eyes. "Talbot!" he yelled. "Get over here!"

"How is Ned?" Castiel asked bluntly, ignoring the small-framed woman who had been skirting around the edges of the room. She took a seat next to Castiel.

"He's worried about his family," the demon admitted. "You're also his family?"

"Yeah," Castiel lied.

"You drop a few pounds recently?" the demon asked.

"It's a juice cleanse," he replied quickly, hoping that omitting a few details would be a sufficient answer.

"Is that the one where you skip the carbs and shoot up on smack?" the demon taunted.

"Can, um—can we just get to it?" Castiel asked uncomfortably.

"You're right," the demon agreed. "Ned's wife and kids should go home."

"Alright, well, what do you want me to do?" Castiel asked, still aching to feel his stress ball back in his hand.

The demon inspected Castiel, as if his eyes were boring into his soul. When he was finished analyzing the situation, the demon added, "Forget it. Get out of here."

"Whatever you need me to do, I can do it—I can!" Castiel argued desperately.

"No, you can't!" the demon shouted, leaning across the desk and slamming his palm on the table. "You're nothing but a damn junkie," the demon said. "I don't want you screwing up and blowing this back in my face."

"Come on, man," Castiel pleaded. "What? Do you want me to kill somebody? I can kill somebody. I've done it before," he attempted to say convincingly.

"You?" the demon asked, his eyebrows raising in skepticism. "You killed someone?"

"Yeah," Castiel replied, setting his jaw and locking eyes with him.

* * *

The team of Omega gathered in the bullpen, listening intently to Castiel's surroundings. Unfortunately, they only had ears on the scene. For auditory observers like Jo and Sam, listening to gain information came naturally. Those were the people Dean despised in high school because of their lack of notetaking. Dean learned better when he could see what was happening in real time, and he could make better decisions based on his visual surroundings.

Rufus shifted uncomfortably beside Dean and asked, "Where the hell is he going with this?"

"I think I know," Benny replied, sitting up straighter and leaning forward to listen with sparked interest.

"Well, if you let his wife and kids go, I'll do whatever you want," Castiel bargained.

"I want you to think very carefully about what you're going to say to me next, Emmanuel," the demon threatened. "I've got friends in law enforcement. I can check details. If you're lying to me, I'm going to know. Sit," he demanded, and Castiel was obligated not to move. "Who'd you kill?"

"I shot a guy while he was sitting on the toilet," Castiel responded, recalling the humorous lie told earlier this afternoon.

"Oh!" Dean exclaimed, catching on to the story. "Nice, Cas!"

"What's so nice about it?" Rufus asked incredulously. "The guy's gonna get himself killed."

"Okay, I need a cold case report entered in," Dean instructed Sam, shrugging Rufus off. "This is gonna be an unsolved homicide, Nashville, two years ago."

"But he's ripping off my story," Sam protested.

"Where did this go down?" the demon probed.

"Nashville, about two years ago," Castiel replied.

"What are you, a mind reader now?" Rufus asked in confusion. "Somebody clue me in."

"The new guy? He's smart," Dean said simply, turning back to Sam and his computer.

"He took my magazines into the head," Castiel explained, drawing from his short-term memory to recall the details.

"I'd kill him, too," the demon remarked.

The lack of emotion in his statement forced a pause from Castiel, and even through audio, Dean could tell he was pushing the conversation. "So I let him get in there and get settled. I walk over to the door. I kick it in, bam. Pop him in the chest. Twice."

"Who's going to fight with pants around their ankles?" the demon asked with a genuine laugh that disturbed Dean to his core.

"Alright," Sam said with finality. "Body found partially clothed in an upstairs bathroom."

"Submit it," Dean ordered. "Let's go!"

"Wait up—they've got some kind of encryption block on the server out in Tennessee," Sam said, fingers hesitantly hovering over the keyboard.

"Just hit the damn send key!" Dean demanded impatiently. "Come on, come on, come on! Let's go."

"So you whacked someone," the demon said bluntly. "Good job. I'll look into the details later. Are you on blood right now?"

"I've been withdrawing for several days now," Castiel replied in a tired, weak voice. He was completely desperate, and his life was at the mercy of a demon. Now Dean was seriously wondering why the poor schmuck didn't quit while he was ahead and go back to a desk job in Sioux Falls. "Please. You—your kind—have to help me. You're the only ones who can."

The demon paused thoughtfully, choosing his next words carefully. "Alright," he agreed. "You help us out, we'll let the woman and the kids go."

"So who's it gonna be?" Castiel said, careful to keep relief from creeping into his voice. "A pro like you?"

"Let's make it a surprise," the demon answered menacingly.

"We're doing this now?" Castiel asked, his heart suddenly racing again.

"Why? You got someplace to be?" the demon answered with another question.

Castiel displayed his indignance quietly, if at all. There was ambient sound for several minutes as the same set of men led Castiel out of the brothel. Dean heard what could only be described as a distorted moan, but considering the setting, it was probably normal. The men were silent, but their message was clear—Emmanuel Allen will do as we say or the family dies.

"So where are we going?" Castiel probed. It was impossible to tell what Castiel was thinking or planning, but Dean trusted him to think on his feet. For a new guy, Castiel went above and beyond the standard. "You know, Horace Greeley would not approve."

"Who is Horace?" Dean asked, perplexed as to the clue Castiel was obviously trying to give them.

"Uh, Horace Greeley," Sam replied matter-of-factly. It almost scared Dean how quickly his younger brother's mind worked sometimes. "Go west, young man. They're taking him east."

Apparently, Castiel didn't see fit to drop any more hints about his location because the rest of the car ride was silent. It was a solid twenty minutes before Dean heard any conversation again.

"Here's the key," Thug One growled. Dean almost snarled in return, until he realized they wouldn't be able to hear him.

"Where'd you get this?" Castiel asked, desperately trying to gain insight into the demonic plan.

"He has a German housekeeper who just happens to be my lady friend," Thug Two said smugly. "It's not your problem. Kill the man in the back bedroom. Be sure he's dead. Fire all the bullets. Bring this back to us."

The man gestured to the gun before handing it to Castiel. He gulped nervously and nodded his understanding, climbing out of the vehicle and trudging down the sidewalk. "I hope you guys can hear me," Castiel whispered as he walked slowly to the building's entrance.

Dean could hear him loud and clear, but that wasn't what worried him. The lack of instructions on Dean's part was what concerned him. He needed to have a serious conversation with Charlie about updating their equipment to a two-way system. Unfortunately, due to limited funds, they couldn't just go out and buy what they needed to rig up spy gear.

"I've got an address," Sam shouted with enthusiasm. Dean mostly ignored Sam's talk of triangulation and satellites, but damn if Dean didn't appreciate his brother's geek-speak in these tricky situations.

"Pull it up," Rufus commanded. "I want backup rolling in that direction now. We need to know what Cas is walking into."

"What are you thinking?" Dean asked incredulously. "We crash this thing with a bunch of hunters rolling in—we lose the family."

"I know," Rufus said darkly. It only took a glance at Rufus for Dean to realize there was no way he would be responsible if they lost Castiel on his first day. They already had a close call earlier, but this should be Dean's primary focus—save Castiel, no matter the consequences.

But Dean knew it didn't have to be like that. He had his slice of pie, and by golly, he wanted to eat it too. "I can get in there," he said, reassuring his statement with a quick nod of his head.

"Yeah?" Rufus asked, inspecting Dean's facial expressions. He realized that Dean wasn't going to back down and that he didn't feel like having this argument. "Go."

Dean darted across the room in a sudden burst of energy. "He's in the building, Sammy," Dean began, resting his elbow on the back of Sam's chair to get a better look at the computer screen. "Tell me something."

"Wait, this house has a government tag," Sam noted, a hint of confusion in his voice. "Some kind of safe house." He began to type feverishly, his hands flying across the keyboard in a frenzy. Suddenly, he came to a halt. "I'll be damned," he breathed in disbelief.

"What?" Dean demanded.

"It's not the government's at all," Sam replied. "It's one of ours." He stopped to think for a second, running through the possibilities. It didn't take long for Sam to come to a conclusion. There was only one safe house in the immediate area belonging to the Men of Letters, and it protected Kevin Tran. His eyes widened in realization. "It's Kevin! They're sending him in to kill Kevin."

"Jo, get Kevin on the phone now," Dean demanded as she quickly took the phone from its hook. This was going to be one hell of a story to tell, if they all survived the night.

* * *

Creaky floorboards had always been a pet peeve of Castiel's. They set him on edge in horror movies and annoyed him to no end in real life. So when the floor made a screech as he stepped on the laminate of the living room, Castiel inwardly cursed himself for not treading lightly.

Fortunately, the young man lying on the couch watching television seemed oblivious to Castiel's presence behind him. His features indicated he was most likely foreign, but Castiel deduced he had lived in the States for most of his life. He couldn't have been more than a graduate student, and he seemed relatively harmless and innocent. Castiel continued to creep closer, this time with much more finesse.

"Excuse me," Castiel tried.

The younger man jerked up from the couch with a blade in his hand, squaring up with the direction of the voice. So much for harmless. "Excuse me?" he asked sarcastically, his eyes darting to the gun Castiel was carrying. "Who are you?"

"I'm not here to hurt you," Castiel promised, though he didn't lower his weapon.

"If that's true, then put the gun down," he said. "Just put it down."

"I wish I could," Castiel replied, still aiming the firearm at the other man's chest.

"Put it down or I'm gonna hurt you this time," the young man responded, expertly maneuvering his knife to a striking position. Unevenly matched with a lesser weapon, it was still clear that this man knew how to effectively defend himself. Castiel refrained from shooting because he didn't want to kill this man. He was simply relying on backup from the Men of Letters to get him out of this situation.

"I can't," Castiel said.

"Who are you?" the young man asked again, setting his sights squarely for the intruder's chest.

"I'm Castiel Novak, Man of Letters," he answered calmly, hoping against hope that the man didn't have an affiliation with the Letters. Being public enemy number one for a local group of demons definitely meant you knew your way around the supernatural world. Castiel assumed that he would at least understand the concept of hunters.

"Let's see some I.D," the young man suggested, motioning with his blade. Clearly, he knew what the Men of Letters were. Castiel noted that his first instinct wasn't to strike, and assumed he had positive feelings associated with them.

"I don't have one," Castiel replied, desperately grasping at straws for a way to prove his loyalty as a Letter.

"Bad day for you," the young man said snarkily.

"I'm undercover," Castiel explained quickly. "Cut me a break, man. It's my first day."

"Who sent you?" he inquired. "The vampires?"

"What?" Castiel asked in confusion. "No, there are demons outside this house right now, and they sent me in here to kill you," Castiel assured him.

"Bastards." He swore again under his breath, and suddenly the phone began to ring. The man ignored the sound and let it go to voicemail. "They aren't even gonna finish me off themselves."

"Wait," Castiel said, pausing for a minute to collect his thoughts. He was a local hunter who seemed to be under house arrest, and he was wanted dead by multiple supernatural groups. All the evidence pointed only to one solution. "You're Kevin Tran?"

"And you're a lousy hitman," Kevin noted sarcastically. "Yeah, I'm Kevin Tran."

Castiel immediately holstered his weapon, fumbling for something useful to do with his hands. Kevin lowered his knife as he did so. "Well, hi, nice to meet you. I'm your new roommate," Castiel said, extending his hand awkwardly. Social situations had never been Castiel's strong suit.

"You're at Omega," Kevin said, his voice raising at the end as though even he wasn't sure if it was a question or statement.

"Yeah," Castiel agreed, dropping his hands back down to his sides. The phone began to sound again and vibrate against the coffee table. "You might want to take that."

"What did you take out of my room?" Kevin asked suspiciously.

"Uh, nothing. Meg she told me not to unpack," he explained. "Come on, you've got to believe me. It's my first day."

Kevin nodded, glancing down at his phone and accepting the call. He knew immediately who it was. "Hey, Jo, it's Kevin. Met the new roommate, Castiel. Almost sliced-n-diced him."

"Almost," Castiel shouted in affirmation. There was a sigh of relief on the end of the line and he thought he heard something to the effect of, "Be ready, Winchester's coming."

"I got to finish this," Castiel said quickly, acknowledging the time on Kevin's phone. "If Dean is coming, I've got to go."

"Yeah, I understand," Kevin replied. "Don't want to piss Papa Bear off, that's for sure."

Castiel withdrew his gun again, but this time he aimed for the floor and emptied his clip as he was told. "I'll see you later," Castiel said as he bolted out the doorway, ignoring the same creaking steps on the way down.

As soon as he reached the steps outside the building, Castiel hustled over to the curb where the burly men were parked.

"You didn't tell me he was a damn Man of Letters!" Castiel yelled emphatically. "He took two shots at me!"

"Is he dead?" Thug One asked bluntly.

"Yeah, he's dead," Castiel replied. Blunt. He could work with blunt.

"Gimme the gun, and get in the car," Thug Two demanded from the backseat.

"Alright," Castiel agreed. "Did you let the wife and the kids go?"

"Yeah," Thug One replied in a tone that told Castiel nothing had been done to release the family. "Get in the car."

"Yeah, you know what? I think I'm gonna walk," Castiel tried to bargain. "The neighbors heard the shots."

"Get in the car," he ordered again, this time more harshly.

"Why do you want him to get in the car?" a familiar voice inquired theatrically from behind.

"Don't be stupid," Thug One said, looking dismissively at Dean. Then he turned to Castiel again. "This is your last chance. Get in the car."

"Or what?" Dean threatened. Thug One reached for something in the floorboard, but it was never revealed to Castiel because Dean shot the man in the temple.

"Ugh! Rufus, if you can hear me, we need an ambulance over here right now," Dean said into his personal transmitter. "My guess is that they get you to kill Kevin, they take you out somewhere, shoot you, make it look like a suicide, then if he ever talks, they make sure somebody finds your gun."

"This is news to me," Thug Two said, still smiling arrogantly.

"Hey! You in the back, show me your hands," Dean demanded. Direct statements, Castiel recalled from his seminars, are the best way to handle contrary offenders. Whether they are rabid creatures or sentient human beings, that was similar. Of course, manipulation tactics potentially work better for humans, but he liked to save those skills for a rainy day.

"Now come on, guys," Thug Two replied, avoiding the order. "It's all cool."

"Do it!" Dean barked, squarely pointing his firearm at the other man's chest.

"Just do what he says, alright?" Castiel asked feverishly. "Do it now!"

"I'm okay, thanks," he persisted.

"Just put your hands up, okay?" Castiel continued. He knew what would happen if this man resisted once more. "Just do what he says."

Before the man had a chance to act, Dean had already fired an unflinching shot straight to the heart. Castiel stood dumbfoundedly blinking at the scarlet staining the man's lapel. Where Castiel was highly trained in the theory of threats, Dean had experience in the practical realm of promise. The way he saw it, there isn't much point in drawing a weapon if you aren't going to use it. Better to put a round through a monster's head than be dinner, that was for sure.

"What? How did you—?" Castiel attempted to ask how he knew what was going to happen. "You saw the gun?" he finally spit out.

"I see it right there," Dean said simply. As it turns out, shoot first, ask questions later isn't always such a bad idea.

"This is Castiel Novak," he said, speaking into his transmitter. "Shots fired. Two men down... Dean Winchester just saved my life."

* * *

"Don't let it go to your head, Cas," Dean said jokingly. They were seated in a lovely office answering pointless—but mandatory—questions to clarify what both testimonies support. Dean would never understand the thoroughness of the Men of Letters. Always questioning, always reasoning. Well, Dean had news for them: As much as he respected the enlightened way of thinking, you can't always logic yourself out of a situation.

"No, sir," Castiel replied. "We did well, though."

"Hell yeah, we did good!" Dean affirmed.

"The driver made a move to his weapon, and that's when Mr. Winchester fired?" the woman clarified.

"Yes, ma'am," Castiel answered politely.

"And you both ordered the man in back to show his hands, and instead he drew his weapon?" she continued.

"Correct again," Dean said dryly.

"Mr. Novak?" the woman asked.

"Yes, ma'am," Castiel said.

"Sounds like a clean shoot to me," she noted. "Excellent work, both of you."

"Thank you," they responded in unison.

As soon as they were out of the stuffy government building and back in the Impala, Dean shrugged off his nice jacket and exchanged it for a leather one in the backseat. He sighed as he sank into the comfortable material. Castiel would never understand how someone so genius could be simultaneously relaxed and informal.

"I hope you like parties, Cas," Dean said knowingly. "Because tonight, we are all about the liquor."

"I'm sorry," Castiel apologized. "We're celebrating our safety by ruining our livers. I just don't see the point in alcoholic beverages, Dean."

"Eh, don't worry," Dean shrugged as he turned the ignition of the Impala. "Spend enough time around me, I'll gladly remove the stick from your ass."

"I don't have a—you know what? Nevermind," Castiel said finally.

"See?" Dean said with a devilish grin. "I'm convincing, aren't I?"

* * *

"Alright, glasses up, everyone!" Sam shouted, raising his glass high as he made the heartfelt toast. "As rookies, we all dealt with demons. But today was one to remember. Cheers!" It was concise, but that didn't make a difference to Castiel. It was meaningful, and that was enough.

"Cheers!" everyone shouted in unison. Dean and Benny smashed their glass mugs together and downed the acidic substance within. Even Meg seemed to rejoice at Castiel's safe return.

"Hey," Dean said sincerely, nudging Castiel with his elbow. "I wanna let you know that no matter how much bitching Rufus does, you did good today."

"Thank you," Castiel replied with gratitude. "That means a lot."

Dean gave a forced smile, and asked, "Cas, can I talk to you outside for a minute?"

To everyone else in their personal pow-wow, it probably seemed strange, but hardly suspicious. To Castiel, Dean's request for a private conversation meant that his purpose for joining the Omega team was about to be revealed. Dean could have all the keys to unlocking the answers of his mission.

"Uh... yeah," Castiel decided, standing to follow Dean up the staircase and to the door of the bunker. As soon as they were out of earshot from the rest of the team, Castiel asked, "What's with the secrecy?"

"Well, you know, Cas, you're a Man of Letters now, okay?" Dean said with confidence. "That means from this moment on, your lies are your life."

"Yes, sir," Castiel affirmed, unsure of where the conversation was now headed. He had survived an entire day in Lebanon. Surely, Dean would humor him and get a move on with telling him the assignment.

"You know, you're out on the street," Dean continued, ignoring Castiel's need for instructions. "You meet some fine little lady or fella—hey, I don't judge—you'd better lie to them. You know, an old friend calls you and asks, "Hey, Cas, what are you working on?" You lie to them."

It had become apparent to Castiel that Dean wasn't just stalling. He was truly unaware. Even in light of this realization, Castiel couldn't believe Dean Winchester could be so cynical and heartless about honesty. Maybe it was just an effect of growing up on the job or seeing so much evil in the world. But maybe it was something much bigger and deeper than that...

"How do you do it though?" Castiel asked helplessly. "I mean, the lies. How do you just keep from going crazy, you know?"

Dean hesitates, staring off into the distance for an uncomfortable moment. Just when Castiel is ready to fill the void of silence with more chatter, Dean responds. "Who says I haven't?"

"No one," Castiel replied truthfully. He recalled his conversation with Jo about how something had changed in Dean after he took a leave of absence. Whatever happened to him during that break from hunting had altered him greatly. Suddenly, Castiel felt a vibration in his pocket and his phone began to ring. "Mind if I take this?"

"Hey, it's your party," Dean consented, turning to leave. "I'm going back inside."

"Thanks," Castiel said graciously, waiting until the door was shut to answer the phone. "Hello?"

"Castiel Novak," a familiar voice echoed over the phone.

"Mister Campbell," Castiel noted, wondering why someone so high on the chain of command would be compelled to call him this late of an evening. "You were right. There's no way I could've predicted this."

"Ah, you actually listened to my speech."

"I did," Castiel admitted, though he spared him the small detail of barely paying attention at his commencement. "Dean Winchester saved my life."

"That so?" he asked.

"Yes, sir," Castiel confirmed. "He did."

There was a moment of silence, and Castiel waited expectantly for him to reveal the real reason why he was assigned here. The man on the other end of the line took a deep breath and began, "I'm calling to let you know that your assignment is to investigate Dean Winchester." If Castiel didn't know any better, he would have thought he stopped breathing entirely. "Will what he did affect that ability?"

He thought for a moment. There was nothing more important to Castiel than duty and obedience. "No, sir," he replied.

"Good," Samuel said tersely. "Keep that attitude, and you'll still make deputy director one day."

"I appreciate that, sir," Castiel stated. "Thank you."

With that, the call ended, leaving Castiel wondering if he made the right decision or not. Did he really have the gall to investigate someone so close to him? Even after a single day together, everyone here was family. Castiel didn't doubt their loyalty to each other or that he would share that same loyalty soon. But then again, could he really defy a direct order?

In his confusion, Castiel trudged back inside slowly. After all, they were expecting him to be at his own you're still alive party. As he entered the bunker once more, Castiel was greeted by the clinking noise of glass against glass and animated chatter. It was as if the whole world was oblivious to his newfound predicament—which of course, it was.

"You know, uh, I heard they kinda slammed you with this job, Cas," Jo began, sidling up next to Castiel and motioning for him to sit down amongst the others.

"Yeah," Castiel agreed as he took a seat next to Sam on the couch. "Yeah, they did."

"No idea why?" Dean asked, staring at him expectantly as if he would reveal something important.

Castiel no longer knew if he could trust those deep green eyes boring into his soul. He couldn't count on anyone in this house to trust him or supply him with information until Castiel proved he was a team player. He had to challenge himself to step away from his individual approach to things and learn to work as one. This cohesive familial unit was the only weapon in his arsenal, and Castiel was determined to make it count. After all, it was Dean who had told him that from this moment on, his lies were his life...

"No, sir," Castiel replied.


	5. Chapter 5

Castiel really had no idea why he bothered listening to Dean anyway. Because of his innate desire to follow orders, he found himself lying on the table of the library with the lights dimmed, attempting a relaxation technique Dean called "finding your spirit dolphin." Under ordinary circumstances, Castiel would feel obligated to give Dean a piece of his mind on meditation, but he was still feeling shell-shocked from his conversation with Mr. Campbell the previous night.

"Cas, what do you see?" Dean asked philosophically. Castiel knew he was supposed to close his eyes and actually try to relax, but in lieu of recent events, he couldn't bring himself to do it. "What do you feel?" he continued. "What do you think?"

"You know, I'm thinking this might not be working," Castiel said, heaving a sigh and sitting upright on the table.

"Okay, fine. We'll try again later," Dean relented, moving to turn the lights back on. "You know, I was a skeptic, too. I'm not exactly a sharing-and-caring kind of person, but a few months ago..." Dean stopped for a moment, and once again, Castiel found himself wondering why Dean would keep a big secret around here. It was their job to observe and seek out liars. It was miraculous that the ugly truth hadn't found its way out yet. "I found it very helpful," Dean finished.

"Yeah? How's that?" Castiel pressed. He was hoping to gather as much information about Dean as possible.

"First thing you gotta do is figure out who the new Cas is in this world," Dean explained, climbing on the table to sit next to Castiel.

He tilted his head in confusion and asked, "New Cas?"

"Yeah," Dean affirmed. "Man of Letters, Castiel Novak, can never be seen here, that's for damn sure. The people in this town must always see you as someone else."

"Ah," Castiel said, nodding his understanding. "And who do they think you are?"

"Everyone thinks I'm Dean," he replied obscurely. "That I like classic cars, and that I'm into rock and roll."

"That's it?" Castiel asked.

"And whiskey," Dean added.

"It's sounds...," Castiel contemplated word choice for a moment before adding, "Vague."

"Vague is good," he responded. "Details invite questions. Questions are what can burn Omega."

Castiel didn't understand why questions could burn Omega, but he thought it wise not to question Dean's authority. Suddenly, a door slammed from down the hall, and Dean jumped to the floor to see who it was.

"Hey, y'all, I'm back," Benny hollered as he marched past the kitchen and into the library to join them.

"Benny," Dean noted, a twinge of disappointment in his voice. Perhaps he was expecting Jo instead. The two of them seemed like they had a history together, though Castiel hadn't yet determined what it was. "What's up?" he asked.

"Nothin'," Benny replied. "Jus' went out for groceries. Whatcha doin'?"

"Working on the new Cas," Dean explained.

"That sounds like a lot of work, brother," Benny said as he set the paper bag of groceries down. "You boys up for a little Makin' Bacon?"

"Hell yeah," Dean responded.

"What's Makin' Bacon?" Castiel asked. Being the new kid on the block meant he didn't know the lingo of their inner circle.

Dean and Benny looked at each other, an unspoken brotherly agreement that they needed to show Castiel the ropes. "What's Makin' Bacon?" they asked in unison. Castiel chose to ignore the condescending tone in both of their voices. It drove him insane being the incompetent one of the group.

About fifteen minutes later, Castiel found himself sitting at a table in Lebanon's finest barbecue restaurant. It was a hole-in-the-wall kind of place with the wait-staff still in either high school or college.

Dean whistled in a low pitch as a young waitress walked past. Benny elbowed him and whispered, "Jail bait." He only responded with a click of his tongue and said, "It's too bad you can't tell around here."

Castiel assumed it wasn't his place to defend the young waitress. It wasn't her fault she needed extra money to help with the bills and tuition. The last thing a girl like that needed was Dean Winchester hitting on her. Castiel bit his tongue to keep himself from saying something he would regret. At the very least, Dean had decided against the unwise decision.

"Hey, Kit," Dean exclaimed as an older lady approached their booth ready to take their order.

"Hey, there, Dean," the woman replied with a friendly Southern accent to rival Benny's. "We missed seein' ya 'round here."

"Yeah, well, that's the job," Dean said with a short glance at Benny and Castiel. "You go where it takes you," he added.

"Well, we're glad to have y'all back!" Kit exclaimed as she uncapped her pink pen. "What can I get for you boys today?"

"Could we git three sweet teas 'n three beef brisket sandwiches wit' a side of baby 'taters?" Benny asked politely, his accent becoming more pronounced to Castiel in the presence of another southern drawl.

"Sure thang, darlin'," she answered as she scrawled out the order. "Ya want them onions caramelized on yer sandwich?"

"Yes, ma'am," Benny replied.

"Okie dokie," Kit said as she finished writing. "It'll be out in jus' a minute."

Dean waited a few moments until she was out of earshot and said, "I like her. She says okie dokie."

"How do you know her?" Castiel asked out of curiosity.

"She's the manager around here," Dean explained. "Keeps all these crazy kids straight and knows just about every customer who stops in here."

"Oh," Castiel responded lamely. It should have been obvious that she wasn't an ordinary waitress. That job seemed to be reserved for young people to make some spare cash.

"You ever tasted barbecue so good you saw God?" Benny asked him.

"Can't say I have," Castiel replied.

"Oh, my brother, you're 'bout to join a cult," Benny said enthusiastically.

Castiel nodded in agreement. This place must be something special for Dean and Benny to give such high ratings. Castiel's sight wandered to the door, and he watched closely as a shady man approached the register. His eyes darted around quickly as though he was surveying for security. When it seemed there was none, he lunged for the bags of potato chips laying on the table and darted for the door. That was a whole new level of low.

"Hey! You have to pay for that!" Castiel shouted as he shoved his chair backwards to chase after the man. A bell chimed as Castiel hit the door full-throttle, and raced down the sidewalk after the man. "Hey!" he yelled. "Get back here!"

"Stop! Stop!" Benny called from the restaurant entrance almost a block behind him. "What the hell are you doing?"

Dean and Benny apparently followed had followed Castiel outside, though he couldn't tell if their intentions were to stop him or the thief. Dean jogged to where Castiel had stopped on the street corner.

"Easy, Cas," Dean demanded in the tone of voice you would use to call off a guard dog. "Are you kidding me right now? Just take it easy."

"But he's getting away!" Castiel protested, gesturing wildly around the corner, in the direction he assumed the thief had ran.

"Yeah, that's right," Dean replied nonchalantly. "Take it easy. What the hell were you gonna do, flash your fake badge and cuff him? Then what?"

"What choice did I have?" Castiel asked incredulously. "He stole from an honest business. That doesn't sound wrong to you?"

Dean took a deep exasperated breath and said, "Right. Right. And because we're Men of Letters, we're in charge if someone breaks the law."

"That's exactly right!" Castiel agreed in his defense, not registering the sarcasm in Dean's voice. "The Men of Letters field guide clearly states that we must engage if we witness an unlawful act. Why aren't we going after him?"

"Screw the book," Dean responded in a deadly serious manner. His facial expression hardened as if it was stone. "It wasn't written for you, okay? You're an undercover civilian. That means your cover is everything. Especially here. This," he motioned to everything around them, "is our home."

"You almost killed business for Makin' Bacon," Benny said with a click of his tongue.

"Well, he was robbing Makin' Bacon!" Castiel replied defensively.

"Cas, this is reality!" Dean snapped. "If we pulled out a gun on every single crime we saw, Omega would go under in a week."

Castiel wordlessly nodded as he trudged along the sidewalk back into the restaurant with Dean and Benny. It made him wonder how many criminals Omega had let go simply because they weren't a supernatural threat. His mind began to spin, unfurling the possibility of Dean's disloyalty to the Men of Letters. Castiel wondered whether it was disloyalty if he was only working for the greater good. There was something about this job that made Castiel endlessly question his morals. How far would he be willing to go to see true justice? Furthermore, how many lesser evils would he be willing to disregard to eliminate the bigger threats?

Benny cleared his throat, cutting through the tension of silence. "Go join the local cops if you want to catch a chips thief, brother." At least he could always count on Benny to lighten the mood.

The next day, Castiel wasn't any closer to figuring out his internal dilemma. In fact, he was more confused than ever in evaluating his morals. Fortunately, his cohorts at Omega distracted him with their own problems, and in Jo's case: kept him fairly entertained.

"Mornin', sunshine," Benny hollered as soon as Jo trudged into the kitchen.

"Too happy. Too loud," she moaned, wincing at the bright light overhead. "Didn't you get enough running in yesterday?" Jo asked in Castiel's general direction.

He glanced down at his workout clothes, far from the formal attire and tan trench coat that was typical of him. Castiel suspected Jo was still seeing double and did her a favor by snatching a pair of sunglasses from a nearby table. "You heard," Castiel said as he passed them to her.

"Of course we heard," Jo replied as she gratefully accepted the shades and put them on. "There are no secrets at Omega," she added.

"Morning, Jo!" Dean said loudly as he entered the kitchen.

"Oh!" she shouted as Dean pecked her on the cheek. There was definitely something going on between those two. "God, you're so loud," Jo grumbled.

"Yeah, I wish I could say her walks of shames were rare," Dean said in a teasing tone.

"This's not a walk a'shame," Jo slurred defensively. "This pathetic thing you see before you is the price of being up all night with a local guy who likes Jagermeister and Dubstep."

Dean grimaced and almost growled at the mention of Jo staying out all night with another guy. "You know there's a really good cure for a hangover," he taunted with a smirk. This was a new side to Dean—the jealous and ferocious alpha male side. "A greasy pork sandwich served up on a dirty ass tray."

"Ugh," Jo groaned. "I hate you."

"I know you do, sweetheart," Dean replied snarkily. "What you get for hanging around Douche-step trash."

"It's Dubstep," she corrected. "And I—"

"Good mornin', y'all," Benny interrupted as he arrived in the kitchen. Castiel was almost grateful for the distraction as Dean and Jo were about three minutes away from starring in a rom com right in front of him.

"What's up, man?" Dean asked.

"Messenger from Sioux Falls dropped that off for you," Benny replied, setting a thick manila envelope on the table.

"Thank you?" Dean guessed.

"Very funny," Benny said sarcastically. "Where's Meg?"

"In her room?" he tried again. "I don't know. It's not my week to keep up with the little liar." Benny sighed deeply as though he wished to say something in Meg's defense.

Personally, Castiel thought her actions were justified. She was only trying to get Kevin back in one piece, and if anything, Meg succeeded in keeping him alive. Nonetheless, Dean Winchester could hold a grudge until Judgement Day, and he was attempting just that.

"Sam," Benny hollered as he began to gather supplies and ingredients in the kitchen. "Gotta couple a pancakes with yer name on 'em, brother."

"I'll take one to go," Sam replied, striding into the room with his laptop and hunting gear in a knapsack. "I've gotta get out of here and get some shifters," he continued as he proceeded to pour a cup of coffee. Castiel noted how alert Sam already was and guessed he'd already been awake for several hours.

Dean nudged Castiel and silently motioned for him to join Dean on the opposite end of the kitchen. When Castiel reached the far corner, he asked, "Is this about yesterday?"

"You think I'm overreacting?" Dean questioned calmly.

Castiel noticed how he chose to answer a question with another question. "Okay, listen," Castiel began. "It will never happen again, all right? I swear on The Men of Letters field guide, which you think I love so much. I will never do something so stupid ever again."

"Never say never," he replied with an air of mystique as he walked back to the island countertop where Benny was making pancakes.

"Hey, Dean, do me a favor," Benny requested. "Open this mail, try not to get anythin' on it."

Dean reached for the mail laying on the countertop and ripped open the first letter. "Uh—First up, psych order, for me, of course." He seemed to take it as an honor to be deemed certifiably insane. "And Mr. Castiel Novak. Poppin' your cherry. Well, I'm not the only one that has to see a shrink," he said with a sarcastic smirk. Sam, Benny, and Jo nodded their approval at Castiel. He no longer saw himself as a rookie. Now there was the matter of convincing Dean.

"If I didn't pull the trigger, why do I need to talk to a psychiatrist?" Castiel asked.

"Doesn't matter," Dean responded matter-of-factly, passing the papers over to Castiel. "You watched two guys get shot by me."

Castiel barely glanced at the letter before deciding it was useless. "Hey, don't tear it up!" Sam exclaimed. "Why not?" Castiel inquired.

"Because you need to go," Jo muttered.

Dean chuckled to himself. "Everybody on our island of misfit toys could use a little head shrinking," he said cynically. "It's at the fake insurance office downtown, okay?"

"Right, on to the next bit of business," Sam ordered, snatching the rest of the papers from Dean's hands like the nosy younger sibling he was. "Hmm," Sam mused aloud. "Looks like they want Cas on one of your actives."

"Awesome," Dean growled. "Give me that," he demanded as he indignantly jerked the papers back from Sam. "Cas. Library. Now."

Castiel obliged to obey Dean's orders and followed him down the hallway to the massive library. "I can do it," Castiel said as they entered the privacy of the library.

"I can't just put you on any case, Cas," Dean tried to explain. "You're too green. Hell, you still have that new-car smell on you." He sniffed Castiel sarcastically just for good measure.

"We kicked ass together with those demons," Castiel argued.

"Mmhmm,"Dean agreed, already equipped with a comeback. "You mean when you almost killed Kevin? Or when Kevin almost killed you?"

"That's not fair," Castiel replied. "Listen, I know your whole case log. Put me on a case."

"How's your Latin?" Dean asked, his tactics becoming more serious.

"Getting there," he responded, avoiding the subject with another question. "What about Lilith? Put me on Lilith."

It didn't take Dean two seconds to answer. "Hell no," he responded.

"I'm up to speed on Lilith," Castiel informed him.

"Up to speed?" Dean questioned.

"She was the first warped soul to fall for Lucifer's ploys—the first demon," he began. "One of the best. Many have studied under her. She's trying to unite all the demons. She's into deals, souls. Never met a vice she didn't like."

"Mmhmm," Dean agreed. "I've been working her for months. You've been in the field less than two weeks. You are not ready. I mean, you almost busted a guy for stealing a bag of chips from a barbecue shop. Do you really think you're ready to be in the field with something seriously supernatural?"

"Come on," Castiel said. At this point he wasn't above begging to work a job. "I was sent down here because Sioux Falls wants me on something."

"That's right," Dean affirmed. "There are too many crimes to count in this city, and I am sure we can find you one with training wheels." Castiel huffed with indignation, but deep down he knew Dean wasn't going to let him on just any case.

It annoyed the living hell out of Castiel that he had to visit a shrink to tell him what he already knew. He was perfectly fine. He could fire a weapon, think clearly, and collaborate effectively with his team—no, his family.

Nevertheless, Castiel found himself approaching the Men of Letters building in Topeka. In the capital of every state, the Men of Letters made a point to have a federal-government-style office disguised as another business. They were usually abandoned armories, or at least the ones Castiel had visited.

Of course, South Dakota's facilities were directly in Sioux Falls. All except for Singer Auto, where the best of the best go to work with Bobby Singer. He wasn't always recognized as a Man of Letters, but many years ago after his wife was possessed by a demon, he threw himself into hunting. There was no other Man of Letters like him. He knew almost every detail of popular lore, and he could scrounge up the uncommon tidbits from his collection of sacred books. Sometimes Castiel wondered if the man ever slept or not.

Other than Sioux Falls, Castiel had been to nearly every Men of Letters facility in the Midwest. Before signing on to accept his legacy status, Castiel had spent a great deal of time hunting with his younger brother, Alfie. Alfie Novak was still in the Academy as he was several years younger than Castiel, but he knew that Alfie would make a fine Man of Letters one day. It took bravery and brilliance to accomplish graduating from the Academy, and Castiel knew from experience that it wasn't easy.

In ordinary school when you mess up, you simply learn and try again later. At the Letter Academy, you didn't just mess up things for yourself. You screwed your whole team over, and they faced the consequences just as if it were their own actions.

In the beginning, Castiel didn't understand why his instructors were so strict, but he learned that in the face of danger, one decision can make or break you. That was reality. Castiel was determined to carve a niche for himself to call his own—to live a life his little brother could be proud of. If that meant visiting a counselor every time he scored a monster kill, he could live with that.

Castiel took the elevator to the top floor where he found an abandoned waiting room and a secretary madly typing into the keyboard.

"Castiel Novak," he said as he approached the service desk. "I'm here to see the doctor, for my after-action evaluation."

"He's expecting you," the secretary answered, barely glancing up from her computer screen long enough to look at him. "Go on in." She gestured behind her where an office door slid open on its own.

Castiel nodded politely and continued into the room with the nameplate Raphael Milton. "Hello, Castiel," a baritone voice warbled from the seat of authority behind the desk. "Have a seat." He motioned for Castiel to sit opposite him in a formal business chair.

"What, no couch?" Castiel asked suspiciously.

"No," the man replied. "Are you disappointed?"

"A little bit," Castiel admitted.

"So...," the man began, reaching for a book set on the shelf behind him. "The Bookkeepers: A Guide to Men of Letters History. It's a good read."

"Do I call you Doctor Milton?" Castiel asked, ignoring the attempts to make him feel comfortable.

"Call me Raphael," he answered simply.

"Okay," Castiel agreed.

"Men of Letters Chairman," Raphael began, opening the manila file on his desk marked with the Aquarian star. "That's the Castiel Novak plan, right?"

"You're reading my file?" Castiel asked curiously.

"It says you requested to be stationed in Sioux Falls," Raphael noted, disregarding Castiel probing assumptions. "Why is that?"

"It's the best place to work your way up," Castiel replied as if the answer were obvious. If a man wanted to become a big-time politician, he would want to spend his time working his way up the corporate ladder at a place like Washington D.C.

"Up to?" he pressed further.

"Maybe chairman," Castiel suggested.

"Why would you want the pressure?" Raphael asked, musing his question aloud.

"I believe there's evil in the world, and I want to fight it and win," Castiel answered strongly.

"You believe in the Men of Letters?" Raphael inquired.

"I do, sir," Castiel replied. For a moment, he wondered if Raphael didn't believe in the Men of Letters. Then what was he doing working for them?

"What got you hooked?" Raphael asked.

"My father. He worked in Virginia, where I was raised," Castiel responded.

"So you're a legacy," he noted, turning back to skimming through the file.

"Well, no, not really," Castiel admitted. "He wasn't a Man of Letters. He was an informant for a hunter."

"Are you disappointed in your assignment to Omega?" Raphael probed. "Sioux Falls is in another state."

"Initially I was, but the bunker is great," Castiel said. "The Letters there are great."

"What about your field training officer, Dean Winchester?" Raphael asked. "Is he great too?"

"He's... complicated," Castiel said finally.

"You say he saved your life that night," Raphael commented.

"He did," Castiel confirmed. "If he didn't pull that trigger, I'd be dead."

"You feel you owe him?" he asked.

"I do," Castiel said firmly.

"How is he complicated?" Raphael questioned further.

"How much time you got?" Castiel mused with a grin. He paused as though thinking of what to say next, but decided to inform Raphael of his deductions. "You're not a shrink, are you?"

"What gave me away?" Raphael asked, opening his hands in surrender.

"Well, there's no "doctor" in front of your name on the door," Castiel began. "That was my first clue. And if you were a shrink, I wouldn't feel like I was being interrogated."

"Let's take a walk," Raphael said, standing a gesturing to the door. "You're observant. I like that."

"Thank you," Castiel said, opening the door and walking alongside Raphael to the silent corridor. "So who are you?"

"I'm your control officer for your investigation into Dean Winchester," Raphael admitted.

"Finally," Castiel exclaimed. "I've been waiting for somebody to tell me what's going on."

"You know, from what I've heard, you're just like him out of the Academy," Raphael told him. "You have the same energy, brains, passion that he had then."

"Why am I investigating him?" Castiel asked in confusion.

"Look, for now just get close to him, become his friend," Raphael said simply.

"Winchester isn't the kind of guy you get tight with overnight," Castiel replied.

"So take your time," Raphael responded. "You're in Omega for the duration. You want to be in that Man of Letters office one day, but you can do it from here. This isn't a detour, Castiel. This is the fast track. You help us with Winchester, and you write your own ticket out of Omega and back to Sioux Falls."

"Blackmail?" Castiel asked with a tone of shock.

"More like incentive," Raphael replied tactfully. "Make him put you on a case. Get in tight with him."

"It's not easy," Castiel said with hesitation.

"That's why we chose you," Raphael answered sincerely, the words ringing in Castiel's ears.


	6. Chapter 6

Chapter 6

Jo Harvelle sat on the edge of her bed, contemplating the decision she was about to make. She had faced this problem for several weeks but ignored it all the same. It was very dangerous for people in this line of business to date their co-workers. Fortunately, she was saved from making a decision by a knock at her door. "Come in," she called.

Castiel peeked around the corner of the door before politely entering. He wasn't wearing the tan trench coat he insisted on wearing, but his white dress shirt was neatly tucked in with a sapphire blue necktie around the crisp collar. Jo drew her legs up to make room for Castiel to sit at the end, and he accepted her welcoming gesture. "Can I ask you for some advice?" he asked as he took a seat.

"Of course," she replied, gladly taking her mind off her own dilemma.

"It's about Dean Winchester," Castiel warned. As if that would stop her from helping Castiel. Dean always seemed to be the focus of everyone's problems around here even if he didn't realize.

Jo sighed. "Of course it's about Winchester," she said.

"I'm trying to get him to put me on something, but he keeps saying I'm too green," Castiel explained.

"He's right. Don't fight him on it," Jo suggested. Castiel stared at her blankly, and she realized how confusing that must have sounded. "Charm him. Dean likes self-starters. You need to bring him something useful."

"Okay, well, there is this guy, Alistair," Castiel began hesitantly. The idea had been brewing in the back of his mind for a while now, but he knew the likelihood of someone listening to him was slim to none. Jo nodded her encouragement and he continued, "He's an up-and-comer Dean is trying to get close to. I thought maybe…"

Jo shook her head and said, "He's just playing the periphery. He hasn't even met the guy. So that means he needs to do something big and splashy in order to get his attention."

"How do I get him to do something big?" Castiel asked in confusion.

"Well, in order for him to get noticed, he needs to give him something he wants but doesn't have," Jo explained as Castiel paid close attention to her suggestions. If he was to succeed as a Man of Letters, he needed to go through Dean Winchester, and Castiel could use as much advice as he could get. "If he was a drug supplier, offer him new territory. If he was smuggling car parts, offer him a cheaper source. You catch my drift?"

"That's the thing with Alistair, though, he seems to be involved in everything," Castiel said, working through the options in his head. Demons were usually interested in anything in the black magic circuit. Maybe Dean would have some ideas if he was on board…

"Good advice?" Jo questioned.

Castiel took a moment to reply, "Yeah, I think so."

"Great," Jo exclaimed, springing from the bed with newfound energy. There was work to be done, and she was a woman with a plan. "Now I need a favor from you. I need a man for a little covert operation."

"Specifically a man?" Castiel asked.

"A man," Jo repeated with a spark in her eyes. "Trust me, it'll be fun. C'mon," she said, grabbing his blue tie to lead him out of the bedroom. Castiel made a mental note to ditch the formal attire as it made for an easy leash.

She led him through the bunker down a back stairway Castiel had never seen before. Now that he thought about it, there were probably parts of the bunker no one had seen before. Nonetheless, Jo eventually brought him to a large room filled with clothes racks and aisles full of wigs and accessories. A vanity mirror sat to the left of the door with a fully stocked shelf of makeup items.

"Welcome to our undercover closet," Jo said with a gesture to the massive collection of outfits. "Stuff the Men of Letters have accumulated over the years. Why toss it if we can use it, right? Especially if we have to travel back in time…" She walked over to the first rack of men's clothing she came to and began to sift through the wardrobe to find something for Castiel. Before he knew it, there was a pile of clothes at Castiel's shoes, discarded in Jo's search for the perfect outfit. "We need to find something to make you look tough," she explained as she continued to rummage through the rack.

"I look tough," Castiel replied dryly, glancing at himself in the mirror and straightening his tie.

Jo spun on her heels to look at him with raised eyebrows. "You do," she said sarcastically. "You totally radiate bad-ass."

"Fine," Castiel relented, loosening his necktie to throw it in the floor amongst the other clothing. "How about gun-toting priest?" he asked, reaching for a clerical collar.

Jo rolled her eyes and elaborated on the costume they were looking for. "Well… tough is the wrong word. It's more like cocky," she explained.

"Is this cocky?" Castiel asked, picking up a pair of aviator sunglasses and sliding them on. "How do I look?"

"Oh, yeah," Jo nodded. "You know who wears sunglasses inside? Blind people," she answered bluntly before adding, "and douchebags." Castiel didn't take offense to the comments. They weren't really his style anyway. Of course, "his style" mostly consisted of formal attire for the office, but that was beside the point. "Hmm, how about this?" Jo asked, holding up a black leather biker jacket with a pair of torn denim blue jeans.

"Alright," Castiel said hesitantly. "Where do I try them on?"

Jo smirked and said, "You lose your modesty awful quick around here, Cas."

"Fine," he said with a sigh as he unbuttoned his top to reveal a white undershirt.

"You might want to trade that for a grey tee shirt," Jo remarked. "With black leather, you'll look too much like a greaser."

"Alright, find me one of those," Castiel agreed, stripping even further to reveal a tan torso and a surprising amount of muscle for such a lean figure. Jo tossed him a dark-colored tee shirt that he gladly accepted. He wasn't the type of person to go around shirtless, and even though he was a bit uncomfortable with how the shirt gripped the curves of his biceps, he could tolerate it.

Castiel shrugged the leather jacket across his shoulders and traded his uniform slacks for the frayed denim jeans picked out. He glanced in the mirror again and ruffled his hair to look the part. "Confident," Jo mumbled as she applied a sangria shade of lipstick. "Not what I was going for, but close enough. Alright, Novak, we're ready to roll," she said as she flipped the light switch and motioned for him to follow.

"Er, where are we going?" Castiel asked as he shut the door behind them.

"To make a delivery to the roommate you haven't met yet," Jo answered, flipping her hair to give it volume.

"We're visiting Charlie?" Castiel questioned further.

"Yeah, you'll like her," Jo said enthusiastically. "Anyway, we're headed to a karaoke bar a couple of towns over. If I go in alone, every jerkoff there starts hitting on me."

"So I'm your boyfriend?" he inquired.

"Temporarily, of course," Jo clarified. She didn't want him thinking any of it was for real-especially with the problem she already had with Dean. "But yeah. My cocky, confident boyfriend," she said with a devilish grin.

When they reached the Men of Letters garage, Castiel was sure they were going to pile into the grotesquely yellow Corvette. Thankfully, Jo headed for a dark Volvo that looked to be the most modern vehicle in the garage. Castiel slid into the passenger seat of the car and shut the door.

"So, what do you want to listen to?" Jo asked as she fastened her seatbelt and turned the ignition. "It's about an hour's ride down to Mitchell County, so you might as well pick the tunes."

"As long as your music isn't as loud and obnoxious as Dean Winchester's, I'm indifferent about what we listen to," Castiel deadpanned.

Jo grinned and said, "You should be glad you're not riding with him, then. I remember my first time in the Impala," she recalled. "House rules, Harvelle. Driver picks the music, shotgun shuts her cakehole."

"Really?" Castiel asked inquisitively. "He was willing to change the cassette tape when I rode with him yesterday."

"I'd like to say he's mellowed out with age," Jo began as they pulled out of the Men of Letters garage. "But the truth is: we really don't know what happened to him last year. The only mystery in this bunker is Dean, and can never quite figure out what that wild card is going to do next."

Castiel was silent, taking time to process the information. He had no clue how to investigate someone this mysterious. Jo cut through the awkward silence by clearing her throat. By now, they had reached the highway, and Jo fiddled with the radio dial until she came across a '90s pop station.

"Don't judge," Jo said pointedly as she placed both hands back on the wheel. "There is a time and place for Zeppelin IV, but a girls' afternoon in my car is not one of them."

"This is a… girls' afternoon, then?" Castiel inquired in teasing tone.

Jo glanced at him from the corner of her eye. "Well," she began. "Undercover case with a fake cocky boyfriend? Definitely calls for the Spice Girls."

The pair of them passed the time listening to Vanilla Ice and Destiny's Child. Castiel found their car ride most amusing, especially when stopped at a crossroads light at which Jo rolled down the windows to jam out to an old pop tune no one remembered. With his contrasting stoic expression, Castiel found many looks of sympathy staring back at him from other cars as he patiently waited for the light to change.

When they finally arrived at the karaoke bar, Jo gave Castiel several last minute reminders. "Remember," Jo said quickly. "Arrogance is everything in here. Stand close, and I'll tell you if PDA is necessary to get someone off my back. Keep your words to a minimum. Swagger is all about good posture, a lazy expression, and a bounce in your step when you walk. You ready?" she asked.

"Ready as I'll ever be," Castiel replied honestly.

As soon as they entered the bar, Castiel knew he had his work cut out for him. Every perverted face in the room turned to undress Jo with their eyes, so Castiel attempted to take a protective stance between her and the rest of the room.

It didn't appear to work, however, because within five minutes, a pasty white man with a suspicious moustache sauntered up beside them. "Hey, honey," the man said in a sultry tone. "Who's the geek?"

Jo flushed her embarrassment and turned away from the man, hoping he would go away if she ignored him long enough. "Mark your territory," she whispered to Castiel when she realized he wasn't moving anytime soon.

"Seriously?" Castiel mumbled in return.

"Seriously," Jo hissed in a low voice. "Mark your territory, and grab my waist."

Castiel uncomfortably reached for Jo's waist and pulled her closer, murmuring something in her ear that sounded vaguely seductive to the man failing to hit on her. The man sighed and turned his attention elsewhere to order another shot from the bartender.

"Easy, tiger," Jo said, pulling away as soon as the man gave up. "Where'd you learn that? On second thought, scratch that. I probably don't want to know. Good job, though. That's what I'm talking about." Jo's attention narrowed to a booth in dim lighting across the bar. Her tone deepened, and Castiel could tell she was totally focused now. "That's Charlie," she said, pointing out a petite red-head on the same side of the booth as another man. "And that's Oberon, King of the Fairies. She's under as his girlfriend."

"What?" Castiel asked incredulously. "Really? Like A Midsummer Night's Dream 'Oberon'?"

"Yeah, but it's a little more complicated than that," Jo whispered heatedly as she stood from the bar stool.

"Why?" Castiel pressed as he stood to follow her.

"Bathroom," she ordered, ignoring his questions. "Now."

Jo suddenly giggled and gave off the presence of a drunken party girl. Castiel was a bit surprised at her ability to change demeanors, but took that as his cue to follow her lead to the bathroom. As they passed Charlie's table, Jo pretended to clumsily trip and fall across their booth.

"I-I'm so s-sorry," she slurred with a hiccup. "A bit too much to drink, I guess."

The small crowd at the booth smiled politely and continued their conversation. As Castiel followed Jo into the women's restroom, Charlie quietly dismissed herself from the table to catch up with them. Once inside, Jo dropped her silly act and checked under each of the stalls to ensure no one could overhear them.

"It's so good to see you," Charlie said in relief as she hugged Jo. "Did you get 'em?"

"Right here," Jo replied, pulling away as she revealed a small plastic bag full of pills.

"I need to start buying these things in bulk," Charlie noted. "So…," she said, turning her attention to Castiel. "This is the infamous Castiel."

"It's Cas," Jo informed her. "He's my boyfriend tonight."

"He's… dreamy," Charlie complimented with a smile. "It's nice to meet you, Cas."

"Er, likewise," Castiel replied, unsure of what to say to her.

"You fresh out of the Academy?" she asked.

"Yes, ma'am," Castiel replied. Despite Jo's attempts to make him look like a tough-as-nails biker boy, he couldn't help but revert back to his manners.

"Still making headway with Oberon?" Jo inquired quickly. From her impatience, Castiel guessed they only had so much time before someone came to check on Charlie in the restroom.

Charlie sighed in despair. "Nothing," she groaned. "I'm two weeks under with him, and all he wants to do is get under me."

"Ugh," Jo snarled in agreement.

"Wait, is that what the birth control pills are for?" Castiel asked in confusion.

"I'm not taking them," Charlie said, shaking her head emphatically.

"And we don't expect her to, either," Jo explained as Castiel's addled expression deepened. "She's not gonna screw a fairy. Or a man, for that matter," she added.

"The pills are for Oberon," Charlie said quickly. "You give a guy a couple of these, and his soldier's at ease." She saluted for effect, and Castiel couldn't help but grin at how brilliant the plan was. Send a lesbian in as a supernatural creature's girlfriend, knowing nothing would cloud her judgement if _that_ scenario would present itself.

"Really?" Castiel asked, his eyebrows raised with interest.

"Really," Charlie confirmed with a nod of her head.

"Well, can I ask you a question?" Castiel inquired. "I mean, you're going under as his girlfriend. Don't you kind of expect him to want to, um, well, you know..." He trailed off in embarrassment. Castiel couldn't quite bring himself to ask about a woman's sex life while she was undercover.

"Absolutely," Charlie answered.

"So, um, why don't you get out?" he questioned.

"Because I want the bastard's head on a platter," she replied with the backbone of a warrior. "Thanks, Jo," she added as she turned to leave their bathroom powwow.

"Good luck," Castiel called after her.

She opened the restroom door a crack before tossing her hair over her shoulder to reply, "It was nice to meet you, Cas."

Charlie's grandiose exit left Castiel staring at how impressive the Women of Letters could be when they teamed up. "Told you that you'd like her," Jo said with a smirk. "Now we need to ruffle that sex hair of yours before we get out of here. If we don't want to raise any eyebrows, you've gotta look like you were getting some in here."

Castiel rolled his eyes before proceeding to tousle his hair and unzip his fly. Jo wiped some of her makeup off and instructed Castiel, "Bite your lip. It'll look like my lipstick rubbed on you."

Jo cracked her knuckles and unbuttoned part of her top before adopting the party girl persona once more and stumbling out of the bathroom dramatically. This was going to be a long afternoon, Castiel thought in exasperation as he followed her lead once more.

In the center of the bunker's library sat Dean Winchester, legs lazily propped up on a table with a book in his lap and a fifth of whiskey to his left. He couldn't concentrate long enough to truly understand what he was reading, but his eyes kept skimming over the same paragraph over and over.

He was finally drawn out of his hazy thoughts by someone entering through the front door. Dean slapped the book together and set his shot glass down on the table.

"What's up, Dean?" Jo asked.

"Nothing much," Dean replied as he rose to meet Jo and Castiel at the bottom of the stairs. "Whoa," he exclaimed. Liquor didn't slow his senses; if anything, drinking made him hyper-aware of everything around him. "Why the hell do you two look like you went a four rounds with Jose Cuervo in the back of a car?" Dean grilled, noting their unkempt appearances.

Jo let out a hearty laugh and explained, "We were undercover. Charlie needed some… assistance in keeping Oberon at bay."

"Oh," Dean said, taken aback by the simple answer. Why was he so concerned with them hooking up anyway?

"So, what have you been up to today?" Jo asked.

Dean sighed and wished he could nurse his shot glass again. "I still haven't met Lilith," he admitted, "but I'm close to one of her lieutenants."

"What's he about?" Castiel inquired, hoping this would be his opportunity to work with Dean on a case.

"A little Jekyll, a little Hyde," Dean explained in his round-about way. Castiel tilted his head in a confused expression, so Dean added, "He's an affable dude, but he'll turn on you in a heartbeat."

"Is there anything your contacts have that Alistair might want?" Castiel asked, taking Jo's advice from earlier. She glanced out of the corner of her eye to see Dean's pleased reaction that Castiel had thought of something that genius.

"I see where you're coming from," Dean conceded, "but not really."

"I think I got something that might help," Castiel said, making up his idea on the spot. All the best plans stemmed from an off-the-wall spark allowed to ignite. Dean nodded as if to say, 'I'm all ears', so Castiel continued, "So one of the things Alistair's looking for is power, right?"

"I see you read my case file," Dean answered slyly.

"Yes," Castiel admitted, "but Sam just scored an alpha a few weeks ago. You think he would be into that?"

"Continue," Dean said simply.

"You tell Alistair that you got a guy at the monster prison with the shifter. A Man of Letters," Castiel explained his idea slowly.

"That'd be you?" Dean asked to clarify.

"I've got the look, right?" Castiel replied. He waited for Dean to agree before continuing, "So we borrow the shifter from Sam and sell him to Alistair. Trap this guy, and force him to give you Lilith's location…"

Castiel trailed off as Dean shook his head in frustration. "Ah, and you started off so strong," Dean commented. "It's too risky. There's too many moving pieces. If word got back to Alistair, I'd be dead. But I appreciate the effort," he added.

"It's a work in progress," Castiel acknowledged the flaws in his plan.

Dean scratched at the slight growth of his beard and sighed. "I'll think about it," he added as he turned back to his whiskey. Castiel smiled as Jo held up her hand for a high-five in the possible victory. It was a maybe, but that was good enough for now.

"Hey, Cas," Jo whispered in a low voice.

"Yeah?" Castiel replied.

"Thanks for helping me out today," Jo said. "I needed to take my mind off a problem, and…," she trailed off for a moment, "you were there for me. Thank you."

Castiel noticed the sentiment in her voice as she voiced her problem aloud. If he was right, her problem involved the one and only Dean Winchester. Not a hard deduction, seeing as every dilemma around here had its roots with Dean. Castiel nodded a short, "You're welcome," before striding back to his room to change out of this monstrously uncomfortable outfit.

A couple hours and a few hundred pages later, Dean found his whiskey bottle nearly three-quarters of the way empty and his eyes crossing too often to focus. The front door opened again, but this time the familiar face was energetic and all too excited to see Dean.

"Hey, stranger," Charlie shouted gleefully from the bunker's entrance.

"Hey," Dean exclaimed in return, greeting her at the foot of the stairs with a big-brotherly bear hug. "What are you doing home?" he asked, finally releasing her from the tight embrace.

"Jo and Cas helped me spike Oberon's drink," she answered with a sly smirk.

Dean chuckled at the news. "The dreaded spike," he said dramatically.

"Mm-hmm," Charlie agreed.

"He couldn't get it up, huh?" Dean asked, grinning at the thought of a big bad who couldn't even get some.

"He got embarrassed and kicked me out," she added, struggling to refrain from laughter.

"You know, at some point, the guy's gonna stop drinking," Dean said pointedly.

"I know," Charlie replied, sighing deeply as though she'd given this thought and couldn't find a suitable answer.

"And then what?" Dean pressed, hoping she would reason her way into a solution on her own.

"I seriously hate working this case," she grumbled. Some would call it whining, but Dean knew Charlie wasn't the type to piss and moan over just anything. "He's not giving me anything. He won't talk business in front of a woman."

"Well, just ease your way out," Dean advised simply.

"I should... But I mean, he's such a pig," Charlie exclaimed. "Why can't men be just be easier to get along with? But you're right. This won't end well for me."

"You know, I still have a connection with Oberon's crew," Dean subtly suggested.

Charlie quickly covered for herself with a, 'No, I-I can't ask you to do that, Dean."

"You know I owe you plenty," Dean said, staring her in the face. She couldn't deny that fact. Charlie had saved his life more times than either of them could count. "And you didn't ask," he added.

She sighed and looked at her shoes in embarrassment. "Thanks, Dean," she said in a small voice.

After carefully deliberating the risks and benefits of Castiel's original plan to get in with Lilith, Dean decided that the endgame outweighed the things that could go wrong. He swallowed and winced at the decision he was about to make final. With a knock on Castiel's bedroom door, Dean heard a reply. "Enter," Castiel said in response to the knock.

"I thought about it, and I think your plan's awesome," Dean admitted. He paused a moment before adding, "We're rolling out in the morning. Best get some shut eye while you can."

"What changed?" Castiel asked, brightening at the acceptance of his plan.

"Mm, told you," Dean said plainly. "I thought about it. Tell Sam," he suggested as he left the room.

Castiel sprung from his bed, jogging down the hallway energetically to find Sam's bedroom. He couldn't believe his stroke of luck. None of this could have happened without Jo's advice. Castiel made a mental note to thank her profusely for her insight. For now, he would concentrate on proving his plan could be a success.

He tapped on Sam's door respectfully, but entered without permission in all the haste of excitement. "Hey, Sam, can I ask you something?" Castiel questioned.

"You just did," Sam replied sarcastically, sitting up straight in his bed. Clearly, he had already retired for the night and Castiel had disrupted his slumber. "Yeah, man, go ahead," he said as he rubbed his eyes to focus his vision.

"Have you filed the paperwork with the prison on that alpha shifter yet?" Castiel asked quickly.

"Er, no," Sam answered.

"Would you mind if I borrowed him?" he pressed further.

"Are you out of your mind?" Sam questioned with a serious face.

"It's only for the day," Castiel added. His tone was just short of begging now, but he needed Sam on his side if he was to pull this off. "Dean can sign for him."

"You think that makes me feel better, knowing my brother has a genius plan?" Sam asked, his voice dripping with sass. "Look, Cas, if he gets out on the streets and happens to take down a civilian, I'll be the Men of Letters whipping boy."

Castiel narrowed his eyes as he realized what it would take to get Sam to agree to this plan. "I'll trade you," Castiel presented. "What do you want?"

Sam sighed and smashed his face into a pillow. "I want you to leave me alone," he moaned.

"I'll do your next round on the chore wheel," he offered. "Sam, come on. Let this shifter do some good in the world before they torture him and send him back to purgatory."

"Alright," Sam conceded, throwing the pillow from his face. "I'll tell you what, Cas. Two. Two turns on the wheel."

"Done," Castiel accepted, backing out of the room before Sam could change his mind. "You're a good man, Samuel!" he yelled in excitement as he shut the door.

"It's Sam," he replied grumpily as he tossed the blanket back over his shoulders.

Early the next morning, the Men of Letters team gathered in the kitchen to gear up with a hearty breakfast and strong coffee-Irish, in Dean's case.

"We got a G. I. Joe in the house, guys," Dean shouted in approval at the appearance of Castiel.

"Reporting for duty, sir," Castiel replied with a small salute. His costume of the day was that of an army brat, and Castiel had to admit the bunker's undercover closet was going to come in pretty useful.

"Right off the legacy recruitment poster," Sam noted

"Reservist at the prison."

"Mmhmm."

"Huntah donated ah shifter for experimentation. He didn't seem ta make it to the prison."

"I dig it," Dean said with a smirk. "Now, look, the boys worked hard to get this backstop for you. If these demons have the ability to check, which I highly doubt, it'll come up that you're registered with the prison in Lebanon, Missouri."

"The Letters have a thing for building in towns called Lebanon or what?" Sam joked half-heartedly.

"Must be," Dean replied.

"So you expectin' to see Lilith today?" Benny inquired.

"Nah," Castiel replied. "It's gonna be Alistair and a few lessah demons that show. Lilith steers clear of this kindah stuff."

"Sure. But what's up with that accent?" Dean asked, noting the Boston twinge in his voice.

"Felt quite natural for the character," Castiel replied.

Dean rolled his eyes as if setting up for a sarcastic comment. "Listen, Jay Leno, if it doesn't flow out of you second nature, you should drop it," he advised. Aside from not knowing who Jay Leno is, Castiel figured constructive criticism was an improvement for Dean, and he should take the suggestion seriously.

"Dropped," Castiel said as his voice naturally slipped back into a deep, resonating Midwestern accent.

"Okay," Dean said approvingly. "Now, we're gonna have audio on both of us. You and I will go in with a couple rounds of ammo, drop the shifter off, and get out of there. We'll make the trade later when the odds aren't so stacked against us."

Dean was interrupted by "Alright, guys, so get this. Found a spot a block away from where you guys are. Closest we can get. No visual inside, though, so no sniper love for you guys."

"Well, what's the signal if something goes wrong?" Castiel asked.

Dean considered the question for a few seconds and replied, "How 'bout we go with son of a bitch?"

"Son of a bitch," Castiel repeated. "That's good."

From the moment Castiel set foot on the warehouse grounds, he knew something was amiss. For starters, they were entering an abandoned warehouse with minimal weapons and no backup. If that wasn't a cause for concern, he didn't know what was. As the pair of them approached the center of the run-down building, Castiel noted Alistair was surrounded by four demons and flanked by a black van with another demon in the driver's seat prepared to make a getaway.

When they were close enough to engage in conversation, Dean greeted him charismatically and started, "This is the guy." He gestured to Castiel standing next to him. "He's a reservist from the Campbell Prison in Missouri."

Alistair glanced over at Castiel as if to size up his prey. "Show me what you brought," he demanded.

"I'll tell you what," Dean began, setting up a deal. "Compared to an alpha, stunt demon number three is going to look like a chew toy. What we have is _the_ alpha shapeshifter. A. K. A. the best known informant to the location of purgatory."

Dean's persuasion intrigued Alistair, but it was up to Castiel to push the deal through. "This shifter is larger and stronger than the ones you're used to dealing with," Castiel added, forcefully arguing their point. High school debate team practice may have actually been good for him, after all. "He may be a tough nut to crack, but I promise you, once he does, you'll have all the intel you'll ever need to that hell-adjacent piece of—"

Alistair interrupted his spiel, less out of agreement and more out the exhaustion of hearing Castiel speak. "Okay, I'll bite," he snapped.

"So we got a deal?" Dean asked with a confident smirk.

"I'll talk to Lilith," he conceded. "But from what I'm seeing… yes, we have a deal."


End file.
